Water → HCID 10891600, compound

Temperature

5 °C

A mixture of trifluoroacetic acid (3.28 ml) and water (6.43 ml) was added to a vigorously, stirred solution of (2S,3R,4S,5S)-3-(tert-butyldimethylsilyloxy)-2-[(tert-butyldimethylsilyloxy)methyl]-4-methoxy-5-methyltetrahydro-2H-pyran (1.0 g, 2.48 mmole) in dry THF (6.43 ml) at 5° C. After vigorous stirring for 25 min at 5° C., the reaction mixture was carefully quenched by the addition of cold saturated aqueous sodium bicarbonate (30 ml). The resulting emulsion was partitioned between ether (50 ml) and water (50 ml). The ether layer was washed with water (20 ml×2), dried over anhydrous sodium sulfate and evaporated to dryness under reduced pressure. The residue was chromatographed on silica gel using AcOEt:n-hexane (2:8) as an eluent to give (2S,3R,4S,5S)-[3-(tert-butyldimethyl-silyloxy)-4-methoxy-5-methyltetrahydro-2H-pyran-2-yl]methanol (0.595 g, 83% yield) as a colorless oil; EI-MS: m/z 290 (M+); 1H-NMR (CDCl3)d: 0.87 (9H,s), 0.97 (3H,d,J=7 Hz), 1.92 (1H,br.s), 2.2 (1H,m), 3.14 (2H,m), 3.28 (3H,s), 3.56 (1H,t,J=9 Hz), 3.57 (1H,dd,J=3 & 11.5 Hz), 3.65 (1H,br,dd,J=6 & 11 Hz), 3.78 (1H,dd,J=2 & 11.5 Hz), 3.84 (1H,br.dd,J=2 & 11 Hz).

1. additionwas added to a vigorously,
2. customthe reaction mixture was carefully quenched by the addition of cold saturated aqueous sodium bicarbonate (30 ml)
3. customThe resulting emulsion was partitioned between ether (50 ml) and water (50 ml)
4. washThe ether layer was washed with water (20 ml×2)
5. dry with materialdried over anhydrous sodium sulfate
6. customevaporated to dryness under reduced pressure
7. customThe residue was chromatographed on silica gel

ORD record

ord-fb20c92a0e77451bb7b38ef98fe380d2

Source dataset

uspto-grants-1998_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05719291