Dimethyl Sulfoxide → HCID 13854278, compound

HRID 2232697Notes

Reaction equation

CS(C)=O.C(Cl)(=O)C(Cl)=O.[CH:11]1([CH:14]([CH2:17][O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([O:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[CH:21]=2)[CH2:15][OH:16])[CH2:13]C1.C(N(CC)CC)C>ClCCl.O>[CH:15]([C:14]1([CH2:17][O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([O:26][C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=3)[CH:21]=2)[CH2:11][CH2:13]1)=[O:16]

Participants

Conditions

Temperature: -70 °C

Procedure

A solution of dry dimethyl sulphoxide (0.87 g) in dichloromethane (12 cm3) was added dropwise to a stirred solution of oxalyl chloride (0.75 g) in dichloromethane (12 cm3) maintained at -70° C. After a period of five minutes had elapsed, a solution of 2-cyclopropyl-3-(3-phenoxybenzyloxy)propane-1-ol (1.45 g) in dichloromethane (6 cm3) was added dropwise, followed by triethylamine (2.3 g) five minutes later. When the addition was complete the mixture was allowed to warm to the ambient temperature over a period of 2 hours. The reaction mixture was poured into water, and extracted with diethyl ether. The extracts were combined, dried over anhydrous magnesium sulphate and concentrated by evaporation of the solvent. The residual oil (1.5 g) was purified by column chromatography using a silica gel column and eluting with dichloromethane to yield 1-formyl-1-(3-phenoxybenzyloxymethyl)cyclopropane (1 g).

Workup

additionWhen the addition
temperatureto warm to the ambient temperature over a period of 2 hours
extractionextracted with diethyl ether
dry with materialdried over anhydrous magnesium sulphate
concentrationconcentrated by evaporation of the solvent
customThe residual oil (1.5 g) was purified by column chromatography
washeluting with dichloromethane

Sources & evidence

ORD record: ord-7ed5d690df994ee796e9b8b9ffa0a7d6
Source dataset: uspto-grants-1988_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04788348

Reaction notes

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