4,4-Difluoro-3-hydroxy-butyric acid ethyl ester synthesis
- Product Name:4,4-Difluoro-3-hydroxy-butyric acid ethyl ester
- CAS Number:145374-00-1
- Molecular formula:C6H10F2O3
- Molecular Weight:168.14
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Yield:145374-00-1 89%
Reaction Conditions:
with sodium tetrahydridoborate in toluene at 20; for 4 h;
Steps:
133.1 Step 1: preparation of ethyl 4,4-difluoro-3-hydroxybutanoate
Step 1: preparation of ethyl 4,4-difluoro-3-hydroxybutanoate. To a stirred solution of ethyl 4,4-difluoro-3-oxobutanoate (10 g, 60.19 mmol) in toluene (300 mL) was added sodium borohydride (2.4 g, 63.2 mmol) portionwise at 0 °C. The resultingmixture was stirred at room temperature for 4 h. The reaction mixture was diluted with water and extracted with ethyl acetate. The combined organic phase was washed with water followed by brine, dried over Na2SO4 and concentrated to provide the title compound as a colorless liquid (9 g, 89%). 1H NMR (400 MHz, DMSO-d6) 6 5.89 (dt, J3.6 Hz, 55.7 Hz, 1 H), 5.81 (brs, 1 H), 4.11-4.02 (m, 3 H), 2.57 (dd, J = 3.9 Hz, 16Hz,H), 2.39 (dd, J = 9 Hz, 15.6 Hz, 1 H), 1.19 (t, J = 7 Hz, 3 H).
References:
WO2014/68527,2014,A1 Location in patent:Page/Page column 166
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