Oxalyl chloride → alpha(R)-Methylcyclohexanepropionic acid chloride

Participants

Reaction Steps

To a solution of α(R)-methylcyclohexane-propionic acid (2.4 g, 14 mmol) in dry CH2Cl12 (30 mL) was added DMF (1 drop) and oxalyl chloride (2 g, 15 mmol). After 2 h at room temperature, the mixture was concentrated. The residue was dissolved in Et2O (10 mL). This solution was filtered. The filtrate was concentrated to provide α(R)-methylcyclohexanepropionic acid chloride as a clear yellow liquid (2.6 g, 98% yield). 1H NMR (400 MHz, CDCl3) 3.02-2.91 (m, 1H), 1.80-1.63 (m, 6H), 1.39-1.10 (m, 5H), 1.28 (d, J=7 Hz, 3H), 0.99-0.85 (m, 2H). This material was used without further purification in the coupling reaction described in the following example.

Provenance & Evidence