Dimethyl Sulfoxide → HCID 22610231, compound

HRID 1860300Notes

Reaction equation

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

Participants

Conditions

Temperature: -60 °C

Procedure

2 ml of oxalyl chloride were dissolved in 100 ml of methylene chloride and treated at −70° C. dropwise with 2.8 g of dimethylsulfoxide. The reaction mixture was warmed for 5 minutes to −35° C., cooled again to −60° C. and treated dropwise with a solution of 2.9 g of (4,4,7,7-tetramethyl-2-pentyl-2,3,4,5,6,7-hexahydro-1H-inden-2-yl)-methanol in 20 ml of methylene chloride. After 15 minutes of stirring at −50° C., 5 ml of triethylamine were added dropwise. The reaction mixture was stirred at room temperature for 3 hours, then poured onto ice/water, extracted with methylene chloride, dried (Na2SO4) and the solvent was evaporated. The yellow, oily residue was purified with flash chromatography (silica gel, hexane/ethyl acetate=20:1) to yield 2.8 g of 4,4,7,7-tetramethyl-2-pentyl-2,3,4,5,6,7-hexahydro-1H-indene-2-carbaldehyde as colorless oil.

Workup

temperatureThe reaction mixture was warmed for 5 minutes to −35° C.
stirringThe reaction mixture was stirred at room temperature for 3 hours
additionpoured onto ice/water
extractionextracted with methylene chloride
dry with materialdried (Na2SO4)
customthe solvent was evaporated
customThe yellow, oily residue was purified with flash chromatography (silica gel, hexane/ethyl acetate=20:1)

Sources & evidence

ORD record: ord-a98bb49da7bd44d49fd6bcfefe64ab4d
Source dataset: uspto-grants-2003_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06528677B1

Reaction notes

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