Dimethyl Sulfoxide → 2-(4,4-Dimethyl-chroman-7-yl)-heptanal

Participants

Reaction Conditions

Reaction Steps

To a solution of oxalyl chloride (0.15 mL) in 9 mL of dichloromethane at −78° C. was added 0.19 mL of DMSO. The mixture was stirred at −78° C. for 5 minutes and then a solution of 2-(4,4-dimethyl-chroman-7-yl)-heptan-1-ol (0.22 g, 0.79 mmole, from Example 1) in 3 mL of dichloromethane was added. The mixture was stirred at −78° C. for 15 minutes then 0.56 mL of triethylamine was added. Stirring was continued at −78° C. for another 15 minutes then at room temperature for two hours. The reaction mixture was quenched by the addition of 20 mL of water, extracted with three 20 mL portions of dichloromethane and the combined organic extracts were washed with two 20 mL portions of water and 20 mL of saturated aqueous sodium chloride solution. The organic phase was dried over MgSO4, filtered and concentrated in vacuo to give a yellow oil. The product was purified by flash chromatography (SiO2, 10% ethyl acetate in hexanes) to afford 0.16 g of 2-(4,4-dimethyl-chroman-7-yl)-heptanal as a colorless oil.

Provenance & Evidence