Dimethyl Sulfoxide → HCID 12972211, compound

HRID 2305935Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[C:9]2[C:4]=1[CH2:5][C@@H:6]([CH3:16])[C@H:7]([OH:15])[CH2:8]2.C(Cl)(=O)C(Cl)=O.CS(C)=O>ClCCl.O.C(N(CC)CC)C>[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[C:9]2[C:4]=1[CH2:5][CH:6]([CH3:16])[C:7](=[O:15])[CH2:8]2

Participants

Conditions

Temperature: -30 °C

Procedure

A solution of alcohol 5 (10 g, 45 mmol) and dichloromethane (200 mL) at −30° C. was treated dropwise with oxalyl chloride (4.92 g, 24 mL, 0.275 mol). The reaction was stirred at −30° C. for 30 min, cooled to −60° C., and DMSO (6.4 mL) was added slowly over 15 min. The reaction was stirred for one hour, cooled to −78° C. for 30 min, and then treated dropwise with triethylamine (40 mL). The reaction was warmed to room temperature and stirred for 1 hr, followed by the addition of water and dichloromethane with thorough mixing. The organic layer was separated, dried with MgSO4, filtered and the solvent was evaporated to an oil. Purification of this material using flash chromatography (flash silica, 70/30: hexane/EtOAc) afforded 6 as a white crystalline solid.

Workup

temperaturecooled to −60° C.
stirringThe reaction was stirred for one hour
temperaturecooled to −78° C. for 30 min
temperatureThe reaction was warmed to room temperature
stirringstirred for 1 hr
customThe organic layer was separated
dry with materialdried with MgSO4
filtrationfiltered
customthe solvent was evaporated to an oil
customPurification of this material

Sources & evidence

ORD record: ord-bcb897060a28457c93681886f7eb7b9a
Source dataset: uspto-grants-2002_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06441049B2

Reaction notes

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