Triethylamine → 2-Bromo-2-methyl-propionic acid 2-(2,2-dimethoxy-ethoxy)-ethyl ester

A solution of 2-(2,2-dimethoxy-ethoxy)-ethanol (2.20 g, 14.6 mmol) from Example 9 in dry triethylamine (3.0 mL, 21 mmol) and dry methylene chloride (30 mL) was stirred at 0° C. 2-bromo-2-methylpropionyl bromide (1.7 mL, 14 mmol) methylene chloride (10 mL) was then added to the alcohol over a 15 minute period. The reaction mixture was warmed to room temperature and stirred overnight. The reaction mixture was filtered, the filtrate was washed with saturated sodium bicarbonate, and dried with magnesium sulfate. The solvent was removed and the yellow oil purified by column chromatography. 1H NMR (300 MHz, CDCl3): δ=1.78 (s, 6H), 3.31 (s, 6H), 3.49 (d, 2H), 3.68 (t, 2H), 4.25 (t, 2H), 4.46 (t, 1H) 13C NMR (300 MHz, CDCl3): δ=31.23, 55.85, 56.15, 65.58, 69.55, 71.44, 103.09, 172.07.

1. filtrationThe reaction mixture was filtered
2. washthe filtrate was washed with saturated sodium bicarbonate
3. dry with materialdried with magnesium sulfate
4. customThe solvent was removed
5. customthe yellow oil purified by column chromatography

ORDレコード

ord-16ef7506915c4bbc8e3d335a930919f5

出典データセット

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08846021B2