Methyl Acetate → Methyl 3-(2-chlorophenyl)-3-hydroxypropanoate

Temperature

-78 °C

Methyl acetate (5.09 mL, 64.0 mmol) was added dropwise to a cold (−78° C.) solution of LDA [prepared at 0° C. from i-Pr2NH (10.5 mL, 74.7 mmol) and 2.0 M n-BuLi in hexane (37.3 mL, 74.7 mmol)] in THF (50 mL). After 45 min, the enolate solution was added via cannula to a cold (−78° C.) solution of 2-chlorobenzaldehyde (3.00 g, 21.3 mmol) in THF (50 mL). The reaction mixture was stirred at −78° C. for 1 h. Aqueous saturated NH4Cl solution (15 mL) was then added and the mixture was allowed to warm slowly to room temperature. The mixture was concentrated under reduced pressure. The residue was taken in Et2O (300 mL) and the resulting solution was washed with water (2×50 mL) and brine (50 mL), dried (MgSO4), filtered and concentrated under reduced pressure. The residue was partially purified by flash chromatography (CH2Cl2:(CH3)2CO, 95:5) to give the title compound (2.9 g, 63% yield).

1. temperatureto warm slowly to room temperature
2. concentrationThe mixture was concentrated under reduced pressure
3. washthe resulting solution was washed with water (2×50 mL) and brine (50 mL)
4. dry with materialdried (MgSO4)
5. filtrationfiltered
6. concentrationconcentrated under reduced pressure
7. customThe residue was partially purified by flash chromatography (CH2Cl2:(CH3)2CO, 95:5)

ORD record

ord-84bf2e78f332446d9676397696c70b40

Source dataset

uspto-grants-2010_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07642277B2