Acetic Acid → 4-(3-Hydroxy-1-octenyl)-5-(1-hydroxy-6-methoxycarbonylhexyl)cyclopentenone

HRID 35489Notes

Reaction equation

C([CH:5]1[C:9](C)(C)[C:8](=[O:12])[C:7](O[SiH3])([CH:13]([OH:23])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19]([O:21][CH3:22])=[O:20])[CH:6]1[CH:26]=[CH:27][CH:28]([O:34][Si](C(C)(C)C)(C)C)[CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])(C)(C)C.C(O)(=O)C.O1CCCC1.C(=O)(O)[O-].[Na+]>C(OCC)(=O)C.CCCCCC.O>[OH:34][CH:28]([CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])[CH:27]=[CH:26][CH:6]1[CH:7]([CH:13]([OH:23])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19]([O:21][CH3:22])=[O:20])[C:8](=[O:12])[CH:9]=[CH:5]1

Participants

Conditions

Temperature: 80 °C

Procedure

370 mg (60 mmoles) of 4-t-butyldimethyl silyloxy-3-(3-t-butyldimethylsilyloxy-1-octenyl)-2-(1-hydroxy-6-methoxycarbonylhexyl)cyclopentanone obtained in Example 22, (1) was dissolved in 10 ml of a mixed solvent consisting of acetic acid, tetrahydrofuran and water in a ratio of 2:1:1, and the solution was stirred at 80° C. for 7 hours. An aqueous solution of sodium bicarbonate and ethyl acetate were added to perform extraction. The organic layers were combined, washed with a saturated aqueous solution of sodium chloride, and dried over anhydrous magnesium sulfate. The dried product was filtered, concentratd, and subjected to silica gel column chromatography (silica gel), 10 g; eluent, hexane:ethyl acetate=5:1→1:2) to give 218 mg (yield 62%) of 4-(3-hydroxy-1-octenyl)-5-(1-hydroxy-6-methoxycarbonylhexyl)cyclopentenone

Workup

extractionextraction
washwashed with a saturated aqueous solution of sodium chloride
dry with materialdried over anhydrous magnesium sulfate
filtrationThe dried product was filtered

Sources & evidence

ORD record: ord-cfed25753ee849999034d0a3121a6967
Source dataset: uspto-grants-1988_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04766147

Reaction notes

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