Dimethyl Sulfoxide → HCID 18349299, compound

HRID 2268113Notes

Reaction equation

C(Cl)(=O)C(Cl)=O.CS(C)=O.[C:11]([C:15]1[C:16]([O:30][CH2:31][CH3:32])=[C:17]([CH:25]2[CH2:27][CH:26]2[CH2:28][OH:29])[CH:18]=[C:19]([C:21]([CH3:24])([CH3:23])[CH3:22])[CH:20]=1)([CH3:14])([CH3:13])[CH3:12].C(N(CC)CC)C>C(Cl)Cl>[C:11]([C:15]1[C:16]([O:30][CH2:31][CH3:32])=[C:17]([CH:25]2[CH2:27][CH:26]2[CH:28]=[O:29])[CH:18]=[C:19]([C:21]([CH3:24])([CH3:23])[CH3:22])[CH:20]=1)([CH3:12])([CH3:13])[CH3:14]

Participants

Conditions

Temperature: -35 °C

Procedure

1.02 g of oxalyl chloride were dissolved in 37 ml of CH2Cl2 and treated with 0.86 ml of dimethyl sulfoxide at −60° C. After shortly warming to −35° C., the reaction mixture was recooled to −60° C. and treated with a solution of 1.2 g of (1RS,2SR)-[2-(3,5-di-tert.butyl-2-ethoxy-phenyl)-cyclopropyl]-methanol in 20 ml of CH2Cl2. After 15 minutes of stirring at −50° C., 1.7 ml of triethylamine were dropped in. The reaction mixture was stirred for 2 hours at room temperature, poured on icewater, extracted with ether, washed (H2O), dried (Na2SO4) and evaporated. The crude material was purified by flash chromatography (silica gel, hexane:ethyl acetate=9:1) and recrystallized from hexane to give 1.01 g of (1RS,2RS)-2-(3,5- di-tert.butyl-2-ethoxy-phenyl)-cyclopropanecarbaldehyde as white crystals, m.p. 96-97° C.

Workup

customwas recooled to −60° C.
stirringThe reaction mixture was stirred for 2 hours at room temperature
additionpoured on icewater
extractionextracted with ether
washwashed (H2O)
dry with materialdried (Na2SO4)
customevaporated
customThe crude material was purified by flash chromatography (silica gel, hexane:ethyl acetate=9:1)
customrecrystallized from hexane

Sources & evidence

ORD record: ord-9ac952edda2e4b6588168e0c3f35f7c3
Source dataset: uspto-grants-2001_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06326397B1

Reaction notes

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