Dimethyl Sulfoxide → HCID 13917420, compound
Reaction equation
CS(C)=O.C(Cl)(=O)C(Cl)=O.[C:11]([O:14][C@@H:15]1[C@@:37]2([CH3:38])[C:19](=[CH:20][CH2:21][C@@H:22]3[C@@H:36]2[CH2:35][CH2:34][C@@:33]2([CH3:39])[C@H:23]3[CH2:24][CH2:25][C@@H:26]2[C@H:27]([CH3:32])[CH2:28][CH2:29][CH2:30][OH:31])[CH2:18][C@@H:17]([O:40][C:41](=[O:43])[CH3:42])[CH2:16]1)(=[O:13])[CH3:12].C(N(CC)CC)C>CCOCC.ClCCl>[C:11]([O:14][C@@H:15]1[C@@:37]2([CH3:38])[C:19](=[CH:20][CH2:21][C@@H:22]3[C@@H:36]2[CH2:35][CH2:34][C@@:33]2([CH3:39])[C@H:23]3[CH2:24][CH2:25][C@@H:26]2[C@H:27]([CH3:32])[CH2:28][CH2:29][CH:30]=[O:31])[CH2:18][C@@H:17]([O:40][C:41](=[O:43])[CH3:42])[CH2:16]1)(=[O:13])[CH3:12]Participants
Procedure
Dimethyl sulfoxide (0.27 ml; 3.81 mmol) was added at -78° C. in an argon atmosphere to 5 ml of a dichloromethane solution of 0.17 ml (1.95 mmol) of oxalyl chloride, and the mixture was stirred for 10 minutes under the same conditions. To the resulting solution was added 3 ml of a dichloromethane solution o 432 mg (0.94 mmol) of 1α,3β-diacetoxychol-5-en-24-ol (1), and the mixture was further stirred for 15 minutes. Triethylamine (1.05 ml; 7.55 mmol) was added to the reaction mixture, and the mixture was stirred for 5 minutes. The temperature of the reaction mixture was returned to ambient temperature. It was treated in a customary manner (extracted with ether). The crude product was purified by silica gel column chromatography [30 g; eluted with hexane/ethyl acetate (5:1)] to give 382 mg of the captioned aldehyde (2).
Workup
- stirringthe mixture was further stirred for 15 minutes
- stirringthe mixture was stirred for 5 minutes
- customwas returned to ambient temperature
- customThe crude product was purified by silica gel column chromatography [30 g; eluted with hexane/ethyl acetate (5:1)]
Sources & evidence
- ORD record
- ord-bcdc20f529914022b6e55cd6efd66c87
- Source dataset
- uspto-grants-1989_05
- Patent number
- US04832875
Reaction notes
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