Allyl bromide → Methyl 2-hydroxy-2-methylpent-4-enoate

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Reaction Steps

To a stirring solution of 2-oxopropionic acid methyl ester (1.0 g, 0.903 mmol), allyl bromide (1.8 mL, 21.32 mmol) in MeOH/HCl (1:4, 10 mL), is added indium powder (1.12 g, 9.76 mmol). The mixture is stirred for 3 days at room temperature. The mixture is quenched with NaHCO3 and extracted with DCM (3×50 mL). The organic layers are washed with water (2×50 mL) and brine. The combined organic layers are dried with MgSO4 and concentrated to afford 2-hydroxy-2-methylpent-4-enoic acid methyl ester: (M+H)+=145.

Provenance & Evidence