Acetic Acid → Methyl 2,2-dimethylchroman-8-carboxylate

Participants

Reaction Steps

To a solution of 2,2-dimethyl-3,4-dihydro-2H-chromene-8-carboxylic acid (300 mg, 1.45 mmol) in methanol (2.10 mL) and toluene (5.20 mL) cooled to 0° C. was added TMS-diazomethane (1.82 mL, 3.64 mmol) dropwise via a syringe. The reaction mixture was warmed to room temperature and stirred for 45 minutes. It was then cooled to 0° C., and acetic acid (2.00 mL) was added carefully. The solvent was evaporated under vacuum and the residue was re-dissolved in EtOAc (80.0 mL), washed with a saturated NaHCO3 solution (20.0 mL, dried over Na2SO4, filtered and concentrated under vacuum. The crude product was used directly to the next step without further purification.

Provenance & Evidence