Carbon Tetrachloride → (S)-methyl3-(benzyloxy)-2-methylpropanoate

An oven dried 1 L single-necked round bottom flask was equipped with a magnetic stir bar and then charged sequentially with 15.948 g (0.135 mol) of (R)-(−)-methyl-3-hydroxy-2-methylpropanoate, carbon tetrachloride (150 mL), cyclohexane (300 mL), and 35.796 g (0.142 mol) of benzyl 2,2,2-trichloroacetimidate. Trifluoromethanesulfonic acid (0.8 mL; 9.0 mmol) was added to the solution and the resulting mixture was stirred for 16 h at room temperature under an N2 atmosphere. The reaction mixture was then filtered and the filtrate concentrated in vacuo. The residue was redissolved in 150 mL EtOAc and extracted with saturated aqueous NaHCO3 (1×100 mL). The organic layer was washed with saturated NaCl, dried (MgSO4), filtered and evaporated. The residual oil was purified on a silica gel flash chromatography column eluted with 10% EtOAc-hexane. The purified fractions were combined and evaporated in vacuo to afford 20.787 (74%) of the title compound as an oil. MS (CI): m/e=209 (M+1).

1. customAn oven dried 1 L single-necked round bottom flask
2. customwas equipped with a magnetic stir bar
3. filtrationThe reaction mixture was then filtered
4. concentrationthe filtrate concentrated in vacuo
5. dissolutionThe residue was redissolved in 150 mL EtOAc
6. extractionextracted with saturated aqueous NaHCO3 (1×100 mL)
7. washThe organic layer was washed with saturated NaCl
8. dry with materialdried (MgSO4)
9. filtrationfiltered
10. customevaporated
11. customThe residual oil was purified on a silica gel flash chromatography column
12. washeluted with 10% EtOAc-hexane
13. customevaporated in vacuo

ORD record

ord-f1a576a24b7246fc884ee7653cfef171

Source dataset

uspto-grants-2001_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06180642B2