A fluorine-containing ether compound represented by R.sup.1—R.sup.2—CH.sub.2—R.sup.3—CH.sub.2—R.sup.4—R.sup.5 is provided. (R.sup.3 is a perfluoropolyether chain; R.sup.1 and R.sup.5 are each independently any one of an alkyl group that may have a substituent, an organic group having at least one double bond or at least one triple bond, and a hydrogen atom; and —R.sup.2—CH.sub.2—R.sup.3 is represented by Formula (2), and R.sup.3—CH.sub.2—R.sup.4— is represented by Formula (3))
-[A]-[B]—O—CH.sub.2—R.sup.3  (2)
R.sup.3—CH.sub.2—O—[C]-[D]-  (3)
([A] is represented by Formula (4), [B] is represented by Formula (5), [C] is represented by Formula (6), [D] is represented by Formula (7), and in the formula, a and b are integers of 0 to 2, c is an integer of 2 to 5, d and f are integers of 0 to 2, and e is an integer of 2 to 5, and at least one of b and d in the formula is 1 or more) ##STR00001##

A fluorine-containing ether compound represented by R.sup.1—R.sup.2—CH.sub.2—R.sup.3—CH.sub.2—R.sup.4—R.sup.5 is provided. (R.sup.3 is a perfluoropolyether chain; R.sup.1 and R.sup.5 are each independently any one of an alkyl group that may have a substituent, an organic group having at least one double bond or at least one triple bond, and a hydrogen atom; and —R.sup.2—CH.sub.2—R.sup.3 is represented by Formula (2), and R.sup.3—CH.sub.2—R.sup.4— is represented by Formula (3))
-[A]-[B]—O—CH.sub.2—R.sup.3  (2)
R.sup.3—CH.sub.2—O—[C]-[D]-  (3)
([A] is represented by Formula (4), [B] is represented by Formula (5), [C] is represented by Formula (6), [D] is represented by Formula (7), and in the formula, a and b are integers of 0 to 2, c is an integer of 2 to 5, d and f are integers of 0 to 2, and e is an integer of 2 to 5, and at least one of b and d in the formula is 1 or more) ##STR00001##

The invention provides a new process for the preparation of treprostinil of formula (I) and its salts using several new intermediates during the building of the ring system.

##STR00001##

The invention provides a new process for the preparation of treprostinil of formula (I) and its salts using several new intermediates during the building of the ring system.

##STR00001##

Provided are a method for producing a terminal conjugated dienal compound without an oxidation reaction and a terminal hydroxyacetal compound useful as an intermediate in the method. More specifically, provided are a method for producing an (E)-dienal compound comprising the steps of: a metalation reaction of an alkynal acetal compound (1) to obtain an organic metal compound (2), an addition reaction of (2) to ethylene oxide to obtain a hydroxyalkynal acetal compound (3), a reduction reaction of (3) to obtain an (E)-hydroxyalkenal acetal compound (4), a functional group conversion reaction of (4) to obtain an (E)-alkenal acetal compound (5) having a leaving group X, an elimination reaction of (5) to obtain an (E)-dienal acetal compound (6), and a hydrolysis reaction of (6) to obtain the (E)-dienal compound (7); and others.

##STR00001##

Provided are a method for producing a terminal conjugated dienal compound without an oxidation reaction and a terminal hydroxyacetal compound useful as an intermediate in the method. More specifically, provided are a method for producing an (E)-dienal compound comprising the steps of: a metalation reaction of an alkynal acetal compound (1) to obtain an organic metal compound (2), an addition reaction of (2) to ethylene oxide to obtain a hydroxyalkynal acetal compound (3), a reduction reaction of (3) to obtain an (E)-hydroxyalkenal acetal compound (4), a functional group conversion reaction of (4) to obtain an (E)-alkenal acetal compound (5) having a leaving group X, an elimination reaction of (5) to obtain an (E)-dienal acetal compound (6), and a hydrolysis reaction of (6) to obtain the (E)-dienal compound (7); and others.

##STR00001##

Provided are a method for producing a terminal conjugated dienal compound without an oxidation reaction and a terminal hydroxyacetal compound useful as an intermediate in the method. More specifically, provided are a method for producing an (E)-dienal compound comprising the steps of: a metalation reaction of an alkynal acetal compound (1) to obtain an organic metal compound (2), an addition reaction of (2) to ethylene oxide to obtain a hydroxyalkynal acetal compound (3), a reduction reaction of (3) to obtain an (E)-hydroxyalkenal acetal compound (4), a functional group conversion reaction of (4) to obtain an (E)-alkenal acetal compound (5) having a leaving group X, an elimination reaction of (5) to obtain an (E)-dienal acetal compound (6), and a hydrolysis reaction of (6) to obtain the (E)-dienal compound (7); and others.

##STR00001##

A composition, consisting essentially of copper, a fluoroalkyl group, and a ligand comprising at least one group-V donor. The molar ratio of copper to the fluoroalkyl group is approximately 1.

A composition, consisting essentially of copper, a fluoroalkyl group, and a ligand comprising at least one group-V donor. The molar ratio of copper to the fluoroalkyl group is approximately 1.

A composition, consisting essentially of copper, a fluoroalkyl group, and a ligand comprising at least one group-V donor. The molar ratio of copper to the fluoroalkyl group is approximately 1.