Water → 3,5-Bis(trifluoromethyl)-alpha-{[2-(trimethylsilyl)ethoxy]methoxymethyl}benzenemethanol

N-Ethyl-N,N-diisopropylamine (465 μl, 2.67 mmol) was added over 2 minutes, to a solution of (RS)-1-[3,5-bis(trifluoromethyl)phenyl]-1,2-ethanediol (Description 3, 488 mg, 1.78 mmol) and [2-(chloromethoxy)ethyl]trimethylsilane (315 μl, 1.78 mmol) in dichloromethane (3 mL) and the mixture was stirred at room temperature for 4 hours, then at 50° C. for 1 hour. The mixture was cooled and dichloromethane (20 mL) and water (20 mL) were added. The layers were separated and the aqueous layer was extracted with dichloromethane (10 mL). The combined organic fractions were dried (Na2SO4) and the solvent was evaporated under reduced pressure. The residue was purified by flash column chromatography on silica gel, eluting with isohexane/EtOAc (90:10) to give the title compound (352 mg, 49%). 1H NMR (400 MHz, CDCl3) δ 7.86 (2H, s), 7.79 (1H, s), 4.96 (1H, m), 4.73 (2H, s), 3.87 (1H, dd, J 11.1, 3.0 Hz), 3.73 (1H, br s), 3.61 (3H, m), 0.93 (2H, t, J 8.5 Hz), and 0.02 (9H, s).

1. waitat 50° C. for 1 hour
2. temperatureThe mixture was cooled
3. customThe layers were separated
4. extractionthe aqueous layer was extracted with dichloromethane (10 mL)
5. dry with materialThe combined organic fractions were dried (Na2SO4)
6. customthe solvent was evaporated under reduced pressure
7. customThe residue was purified by flash column chromatography on silica gel
8. washeluting with isohexane/EtOAc (90:10)

ORD 기록

ord-26ef180a91d445458ac6694f42f4c006

출처 데이터셋

uspto-grants-2005_10

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US06953792B2