Dimethyl Sulfoxide → HCID 131718006, compound

HRID 1588447Notes

Reaction equation

C(Cl)(=O)C(Cl)=O.CS(C)=O.[OH:11][CH:12]([C:39]([F:44])([F:43])[CH2:40][CH2:41][CH3:42])[CH2:13][CH2:14][CH2:15][C@H:16]1[C@H:20]([OH:21])[CH2:19][C@H:18]([O:22][CH:23]2[CH2:28][CH2:27][CH2:26][CH2:25][O:24]2)[C@@H:17]1[CH2:29]/[CH:30]=[CH:31]\[CH2:32][CH2:33][CH2:34][C:35]([O:37][CH3:38])=[O:36].C(N(CC)CC)C>C(Cl)Cl>[F:44][C:39]([F:43])([CH2:40][CH2:41][CH3:42])[C:12](=[O:11])[CH2:13][CH2:14][CH2:15][C@H:16]1[C:20](=[O:21])[CH2:19][C@H:18]([O:22][CH:23]2[CH2:28][CH2:27][CH2:26][CH2:25][O:24]2)[C@@H:17]1[CH2:29]/[CH:30]=[CH:31]\[CH2:32][CH2:33][CH2:34][C:35]([O:37][CH3:38])=[O:36]

Participants

Conditions

Temperature: -50 °C

Procedure

A solution of oxalyl chloride (0.24 ml) in methylene chloride was cooled to -78° C., followed by addition of DMSO (0.44 ml). After 15 minutes, a solution of the diol (41) (0.358 g) in methylene chloride was added dropwise to the resultant mixture. After 30 minutes, the mixture was warmed to -50° C., followed by stirring for 1.5 hours. Then, the reaction mixture was allowed to warm to -35° C. and triethylamine (0.88 ml) was added thereto. The crude product obtained after the usual work-up was subjected to silicagel column chromatography to give the diketone (42).

Workup

waitAfter 30 minutes
temperatureto warm to -35° C.
customThe crude product obtained after the usual work-up

Sources & evidence

ORD record: ord-596ae3fbd6a74fecb2d43ffbaf5bb385
Source dataset: uspto-grants-1993_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05221799

Reaction notes

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