Methyl chloroformate → Methyl 3-(3,5-dimethylphenyl)prop-2-ynoate

Participants

Reaction Steps

1H NMR(CDCl3) δ7.12 (2H,s), 6.98 (1H,s), 3.00 (1H,s), 2.29 (6H, s). 1-(3,5-dimethylphenyl)acetylene (11.3 g, 86.3 mmol) in dry THF (80 mL) was cooled in dry ice/acetone bath under an argon atmosphere. The n-BuLi (1.6M in hexanes, 65 mL, 104 mmol) was added slowly, followed by methyl chloroformate (11.4 g, 9.4 mL, 121 mmol) addition. The reaction vessel was transferred to an ice/water bath and stirred for 1 h. Saturated sodium bicarbonate solution and ethyl ether were added to the reaction mixture. The organic layer was washed with saturated brine, dried (Na2SO4), and concentrated to give crude 3-(3,5-dimethylphenyl)propynoic acid methyl ester which was used for next step.

Provenance & Evidence