Reaktion #1368386

ord-fad99d54c42744ee901d2bdf4a84b925

Reaktionsgleichung

$CCCCCCCC1(CC[C@H]2[C@H](OC3CCCCO3)CC(=O)[C@@H]2C/C=C\CCCCCC(=O)OC(C)C)OCCO1$

compound ( 5-a )

$CCCCCCCC1(CC[C@H]2[C@H](OC3CCCCO3)CC(=O)[C@@H]2C/C=C\CCCCCC(=O)OC(C)C)OCCO1$

isopropyl (Z)-9-[(1R,2R,3R)-2-(3,3-ethylene dioxydecyl)-5-oxo-3-(tetrahydropyranyloxy)cyclopentyl]-7-nonenoate

acetic acid

THF

→

$CCCCCCCC(=O)CC[C@H]1[C@H](O)CC(=O)[C@@H]1C/C=C\CCCCCC(=O)OC(C)C$

titled compound ( 6-a )

Ausbeute 66.0%

$CCCCCCCC(=O)CC[C@H]1[C@H](O)CC(=O)[C@@H]1C/C=C\CCCCCC(=O)OC(C)C$

isopropyl (Z)-9-[(1R,2R,3R)-3-hydoxy-5-oxo-2-(3-oxodecyl)cyclopentyl]-7-nonenoate

Ausbeute 66.0%

Edukte

$CCCCCCCC1(CC[C@H]2[C@H](OC3CCCCO3)CC(=O)[C@@H]2C/C=C\CCCCCC(=O)OC(C)C)OCCO1$

compound ( 5-a )

$CCCCCCCC1(CC[C@H]2[C@H](OC3CCCCO3)CC(=O)[C@@H]2C/C=C\CCCCCC(=O)OC(C)C)OCCO1$

isopropyl (Z)-9-[(1R,2R,3R)-2-(3,3-ethylene dioxydecyl)-5-oxo-3-(tetrahydropyranyloxy)cyclopentyl]-7-nonenoate

acetic acid

THF

Reagenzien

Keine

Lösungsmittel

water

Reaktionsbedingungen

Temperatur

50°CELSIUS

Detaillierte Bedingungen

See reaction.notes.procedure_details.

Aufarbeitung

1
SonstigeThe crude product obtained by the conventional treatment of the reaction mixture
2
Sonstigewas purified on silica gel column

Vorschrift

The compound (5-a)(0.311 g) was dissolved in the solvent mixture (acetic acid:THF:water=2:1:1)(5 ml) and the solution was maintained at 50° C. for 3 hours. The crude product obtained by the conventional treatment of the reaction mixture was purified on silica gel column to give the titled compound (6-a)[yield:0.156 g(66%)].

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US06452039B1uspto-grants-2002_09