2-Dimethylaminopyridine → HCID 56613713, compound

HRID 35491Notes

Reaction equation

[O:1]([CH:9]([CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])[CH:10]=[CH:11][CH:12]1[CH:16]([CH:17](O)[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]([O:25][CH3:26])=[O:24])[C:15](=[O:28])[CH:14]=[CH:13]1)[Si:2]([C:5]([CH3:8])([CH3:7])[CH3:6])([CH3:4])[CH3:3].CN(C1C=CC=CN=1)C.CS(Cl)(=O)=O.C(=O)(O)[O-].[Na+]>ClCCl>[Si:2]([O:1][CH:9]([CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])[CH:10]=[CH:11][CH:12]1[C:16](=[CH:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]([O:25][CH3:26])=[O:24])[C:15](=[O:28])[CH:14]=[CH:13]1)([C:5]([CH3:6])([CH3:8])[CH3:7])([CH3:4])[CH3:3]

Participants

Conditions

Temperature: 40 °C

Procedure

480 mg (1.0 mmole) of 4-(3-t-butyldimethylsiloxy-1-octenyl)-5-(1-hydroxy-6-methoxycarbonylhexyl)-2-cyclopentenone was dissolved in 5 ml of dichloromethane, followed by addition of 730 mg (6 mmoles) of dimethylaminopyridine and 230 microliters (3.0 mmoles) of methanesulfonyl chloride in this order. The mixture was stirred at 40° C. for 2 hours. An aqueous solution of sodium bicarbonate was added, and the mixture was stirred with dichloromethane. The organic layers were combined, washed with a saturated aqueous solution of sodium chloride and dried over anhydrous sodium sulfate. The dried product was filtered, concentrated and subjected to silica gel column chromatography (silica gel 20 g; eluent, hexane:ethyl acetate=10:1) to give 114 mg (yield 25%) of 4-(3-t-butyldimethylsilyloxy-1-octenyl)-5-(6-methoxycarbonylhexylidene)-2-cyclopentenone. The resulting compound had the following spectral data.

Workup

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

Sources & evidence

ORD record: ord-fe1403fc89004298bf00072c68230820
Source dataset: uspto-grants-1988_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04766147

Reaction notes

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