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

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.

1. customThe mixture is quenched with NaHCO3
2. extractionextracted with DCM (3×50 mL)
3. washThe organic layers are washed with water (2×50 mL) and brine
4. dry with materialThe combined organic layers are dried with MgSO4
5. concentrationconcentrated

ORD record

ord-a5d2cbd258884f67a2847b8f97d9344c

Source dataset

uspto-grants-2010_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07700633B2