Methane → HCID 21480145, compound

Temperature

-10 °C

A solution of 2-hydroxy-2-fluoromethylpropionic acid (0.93 g, 7.65 mmol) in dry dimethylacetamide (20 ml) was stirred under a nitrogen atmosphere at -10° C. Thionyl chloride (0.91 g, 7.65 mmol) was added and the resulting mixture was allowed to stir at -10° C. for 1 hour. 4-Phenylsulfonylaniline (1.0 g, 4.29 mmol) was then added and the reaction mixture was stirred at -10° C. for a further 15 mins. The solution was then allowed to warm to room temperature where it was stirred overnight. The reaction mixture was poured onto water, extracted with ethyl acetate, and the combined ethyl acetate portions were washed with water, and brine. After drying (Na2SO4) the ethyl acetate was removed by evaporation to give an straw-colored foam. Chromatography on silica gel, eluting with ethyl acetate/hexane (1:1) gave the tertiary carbinol (0.75 g, 48%) as a white powder; mp=146°-148° C. 1H--NMR (300 MHz, d6 --DMSO): 1.36 (s, 3H, CH3), 4.38 (dd, J=72 and 9.4 Hz, 1H, CH2F), 4.58 (dd, J=72 and 9.3 Hz, 1H, CH2F), 6.32 (s, 1H, OH), 7.56 (t, J=7.7 Hz, 2H, ArH), 7.65-7.76 (m, 5H, ArH), 7.97 (d, J=8.7 Hz, 2H, ArH), 10.08 (s, 1H, NH). MS (CI, CH4): 302(M+1, 100).

1. stirringthe reaction mixture was stirred at -10° C. for a further 15 mins
2. temperatureto warm to room temperature where it
3. stirringwas stirred overnight
4. additionThe reaction mixture was poured onto water
5. extractionextracted with ethyl acetate
6. washthe combined ethyl acetate portions were washed with water, and brine
7. dry with materialAfter drying (Na2SO4) the ethyl acetate
8. customwas removed by evaporation
9. customto give an straw-colored foam
10. washChromatography on silica gel, eluting with ethyl acetate/hexane (1:1)
11. customgave the tertiary carbinol (0.75 g, 48%) as a white powder

ORD record

ord-53055f0f1f034b93b675f89522cb3c8b

Source dataset

uspto-grants-1993_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05272163