Dimethyl Sulfoxide → HCID 17989231, compound

HRID 1443283Notes

Reaction equation

C(Cl)(=O)C(Cl)=O.CS(C)=O.[F:11][C:12]1[C:13]([O:31][CH3:32])=[C:14]([C:19]([CH3:30])([CH3:29])[CH2:20][C:21]([C:25]([F:28])([F:27])[F:26])([OH:24])[CH2:22][OH:23])[CH:15]=[CH:16][C:17]=1[CH3:18].C(N(CC)CC)C>ClCCl.O>[F:11][C:12]1[C:13]([O:31][CH3:32])=[C:14]([C:19]([CH3:30])([CH3:29])[CH2:20][C:21]([OH:24])([C:25]([F:28])([F:27])[F:26])[CH:22]=[O:23])[CH:15]=[CH:16][C:17]=1[CH3:18]

Participants

Conditions

Temperature: -78 °C

Procedure

1.57 g (12.31 mmol) of oxalyl chloride is introduced into 27 ml of dichloromethane and cooled to −78° C. After dropwise addition of 1.93 g of DMSO, dissolved in 5.2 ml of dichloromethane, the batch is stirred for five more minutes. Then, 3.65 (11.26 mmol) of 4-(3-fluoro-2-methoxy-4-methylphenyl)-4-methyl-2-(trifluoromethyl)-pentane-1,2-diol, dissolved in 11.5 milliliters of dichloromethane, is added in drops. After two hours of stirring, the batch is carefully mixed with 6.61 ml (56.28 mmol) of triethylamine. After one and one-half hours of vigorous stirring at room temperature, water is added, and the batch is shaken twice with dichloromethane. The combined organic extracts are washed with 1% sulfuric acid, saturated sodium bicarbonate solution and brine. After the organic phase is dried, the solvent is spun off. 2.79 g (76.9%) of the aldehyde that is obtained, which is further incorporated in crude form, remains.

Workup

additionis added in drops
stirringAfter two hours of stirring
stirringAfter one and one-half hours of vigorous stirring at room temperature
washThe combined organic extracts are washed with 1% sulfuric acid, saturated sodium bicarbonate solution and brine
customAfter the organic phase is dried

Sources & evidence

ORD record: ord-668c48c1fede4814bcd1737ddb2773d8
Source dataset: uspto-grants-2010_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07659297B2

Reaction notes

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