Hydrochloric Acid → 1-Butylcyclobutane-1-carbaldehyde

Participants

Reaction Conditions

Reaction Steps

To 31.6 mL of 2.0 M (63.3 mmol) of oxalyl chloride in dichloromethane was added 100 mL of DCM followed by 9.0 mL (126 mmol) of dimethylsulfoxide under Ar at −78° C. The mixture was stirred at −78° C. for 30 min. To this mixture was added 6.00 g (42.2 mmol) of (1-butylcyclobutyl)methanol in 10 mL of DCM. The temperature was allowed to warm to −40° C. over 40 minutes. To this mixture was added 35.3 mL (253 mmol) of Et3N dropwise. After the addition was completed, the temperature was allowed to warm to 0° C. over 1 hr. Water (30 mL) was added to the reaction mixture. The pH of the mixture was adjusted to ˜6 using 2N HCl. After extraction with DCM (2×100 mL), the combined organic phase was combined, washed with brine, dried (Na2SO4). Concentration afforded 6.0 g of the crude product as colorless oil, which was used directly for next step.

Provenance & Evidence