Dimethyl Sulfoxide → HCID 178520959, compound

HRID 1189475Notes

Reaction equation

C(Cl)(=O)C(Cl)=O.CS(C)=O.[OH:11][CH2:12][C@H:13]1[CH2:18][CH2:17][C@H:16]([C:19]([O:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[O:20])[CH2:15][CH2:14]1.C(N(CC)CC)C>ClCCl.O>[CH:12]([C@H:13]1[CH2:18][CH2:17][C@H:16]([C:19]([O:21][CH2:22][C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)=[O:20])[CH2:15][CH2:14]1)=[O:11]

Participants

Conditions

Temperature: -78 °C

Procedure

Under nitrogen air flow, to a solution of 0.73 mL of oxalyl chloride in 13 mL of dichloromethane was added dropwise a mixed liquid of 1.23 mL of dimethylsulfoxide and 14 mL of dichloromethane at −78° C. First, a solution of 1.70 g of the obtained benzyl trans-4-(hydroxymethyl)cyclohexane carboxylate in 20 mL of dichloromethane was added dropwise to the reaction mixture at −78° C. After stirring at −78° C. for 0.5 hours, triethylamine was added thereto at −78° C., followed by stirring at −65° C. for 2 hours. The reaction liquid was warmed to room temperature, dichloromethane and water were added thereto, and the aqueous layer was separated. The organic layer was washed with water, 1 M hydrochloric acid, a saturated aqueous sodium hydrogen carbonate solution, and saturated brine in this order, and dried over anhydrous sodium sulfate, and then the solvent was evaporated to obtain 1.60 g of benzyl trans-4-formylcyclohexanecarboxylate.

Workup

customat −78° C.
stirringby stirring at −65° C. for 2 hours
customThe reaction liquid
temperaturewas warmed to room temperature
customthe aqueous layer was separated
washThe organic layer was washed with water, 1 M hydrochloric acid
dry with materiala saturated aqueous sodium hydrogen carbonate solution, and saturated brine in this order, and dried over anhydrous sodium sulfate
customthe solvent was evaporated

Sources & evidence

ORD record: ord-b1b9810b20b0481b81c9b752b1a01f05
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08674096B2

Reaction notes

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