Reaktion #1675625

ord-0d5c3181356e45e3ae150e3e14e01df7

Reaktionsgleichung

Collins reagent

pyridine

$CCCC(F)(F)C(O)CCC[C@H]1[C@H](C)CC(=O)[C@@H]1C/C=C\CCCC(=O)OC$

alcohol

$CCCC(F)(F)C(O)CCC[C@H]1[C@H](C)CC(=O)[C@@H]1C/C=C\CCCC(=O)OC$

methyl (Z)-7-[(1R,2S,3R)-2{4(R,S)-hydroxy-5,5-difluorooctyl}-3-methyl-5-oxocylopentyl]-hept-5-enoate

→

$CCCC(F)(F)C(=O)CCC[C@H]1[C@H](C)CC(=O)[C@@H]1C/C=C\CCCC(=O)OC$

titled compound ( 32 )

Ausbeute 81.0%

$CCCC(F)(F)C(=O)CCC[C@H]1[C@H](C)CC(=O)[C@@H]1C/C=C\CCCC(=O)OC$

methyl (Z)-7-[(1R,2S,3R)-2-(5,5-difluoro-4-oxooctyl)-3-methyl-5-oxocylopentyl]hept-5-enoate

Ausbeute 81.0%

Edukte

$CCCC(F)(F)C(O)CCC[C@H]1[C@H](C)CC(=O)[C@@H]1C/C=C\CCCC(=O)OC$

alcohol

$CCCC(F)(F)C(O)CCC[C@H]1[C@H](C)CC(=O)[C@@H]1C/C=C\CCCC(=O)OC$

methyl (Z)-7-[(1R,2S,3R)-2{4(R,S)-hydroxy-5,5-difluorooctyl}-3-methyl-5-oxocylopentyl]-hept-5-enoate

—

resultant mixture

Reagenzien

Keine

Lösungsmittel

methylene chloride

Reaktionsbedingungen

Detaillierte Bedingungen

See reaction.notes.procedure_details.

Aufarbeitung

1
SonstigeThe obtained crude product

Vorschrift

Celite (5 g) was added to Collins reagent prepared from chromic anhydride (1.2 g) and pyridine in methylene chloride (20 ml), followed by addition of a solution of the alcohol (31) (0.138 g) in methylene chloride (10 ml). The resultant mixture was stirred at room temperature for 30 minutes, followed by the usual work-up. The obtained crude product was subjected to silicagel column chromatography to give the titled compound (32).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05221799uspto-grants-1993_06