Dimethyl Sulfoxide → HCID 20448834, compound

HRID 358371Notes

Reaction equation

C(Cl)(=O)C(Cl)=O.CS(C)=O.[Si:11]([O:18][C@@H:19]1[CH2:23][C:22](=[O:24])[C:21]([S:25][CH2:26][CH2:27][CH2:28][CH2:29][OH:30])=[CH:20]1)([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12].[Cl-].[NH4+]>ClCCl>[Si:11]([O:18][CH:19]1[CH2:23][C:22](=[O:24])[C:21]([S:25][CH2:26][CH2:27][CH2:28][CH:29]=[O:30])=[CH:20]1)([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12]

Participants

Conditions

Temperature: -30 °C

Procedure

Oxalyl chloride (48 microliters; 0.55 mmole) was dissolved in 2 ml of dry dichloromethane, and the solution was cooled to -30° C. Dimethyl sulfoxide (78 microliters; 110 mmoles) was added, and the mixture was stirred for 3 minutes. A solution of 158 mg (0.5 mmole) of 4(R)-t-butyldimethylsilyloxy-2-(4-hydroxybutylthio)-2-cyclopentenone in 1 ml of dry dichloromethane was added over the course of 1 minute, and the mixture was stirred at -30° C. for 30 minutes. Then, 5 ml of a saturated aqueous solution of ammonium chloride was added, and the mixture was extracted with dichloromethane. The organic layers were combined, dried over anhydrous sodium sulfate, filtered, and concentrated. The resulting oily product was chromatographed on a silica gel column using hexane/ethyl acetate (5/1) to give 96 mg (yield 61%) of 4(RS)-t-butyldimethylsilyloxy-2-(4-oxobutylthio)-2-cyclopentenone.

Workup

stirringthe mixture was stirred at -30° C. for 30 minutes
extractionthe mixture was extracted with dichloromethane
dry with materialdried over anhydrous sodium sulfate
filtrationfiltered
concentrationconcentrated
customThe resulting oily product was chromatographed on a silica gel column

Sources & evidence

ORD record: ord-2d1225f6b1e14b0e91046915c5171c3e
Source dataset: uspto-grants-1984_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04466980

Reaction notes

Loading…