Triethylamine → HCID 178425539, compound

To a stirred solution of [3-(tert-butyl-dimethyl-silanyloxymethyl)-5-methyl-phenyl]-methanol (11.1 g, 41.67 mmol) in dichloromethane (80 ml) at 0° C. (ice bath), was added triethylamine (8.78 ml, 62.5 mmol) followed by methanesulfonyl chloride (3.87 ml, 50 mmol). After stirring for 2 hr, the reaction mixture was washed with aqueous saturated sodium bicarbonate solution, dried with anhydrous magnesium sulfate, filtered, and evaporated in vacuo. The crude product was then dissolved in anhydrous DMF (80 ml) and sodium cyanide (6.28 g, 128 mmol) was added into the mixture. The mixture was stirred in an oil bath (60° C.) for 2 hr. After cooling to room temperature, the mixture was partitioned between ether and water. The ether layer was taken, washed with water twice, dried with anhydrous magnesium sulfate, filtered, and evaporated in vacuo. The residue was purified by silica gel column chromatography (eluent, EA: hexanes (from 1:20 to 1:10)) to afford 8.36 g (73%) of a white solid. m.p. 52-54° C.; 1H NMR (200 MHz, CDCl3) δ 0.12 (6H, s), 0.95 (9H, s), 4.2.35 (3H, s), 3.71 (2H, s), 4.71 (2H, s), 7.03 (1H, s), 7.08 (2H, s).

1. washthe reaction mixture was washed with aqueous saturated sodium bicarbonate solution
2. dry with materialdried with anhydrous magnesium sulfate
3. filtrationfiltered
4. customevaporated in vacuo
5. dissolutionThe crude product was then dissolved in anhydrous DMF (80 ml)
6. stirringThe mixture was stirred in an oil bath (60° C.) for 2 hr
7. customthe mixture was partitioned between ether and water
8. washwashed with water twice
9. dry with materialdried with anhydrous magnesium sulfate
10. filtrationfiltered
11. customevaporated in vacuo
12. customThe residue was purified by silica gel column chromatography (eluent, EA: hexanes (from 1:20 to 1:10))

ORD record

ord-b4c1796e07844b18a4264f0069f91864

Source dataset

uspto-grants-2012_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08106064B2