Propanoic acid, 2-bromo-2-methyl-, ethyl ester → HCID 59268005, compound

A solution of 2.79 g (13.45 mmol) of 1-{[(2S)-oxan-2-ylmethyl]sulfanyl}ethan-1-one in ethanol (60 mL) is degassed with nitrogen over 0.5 h and 1.51 g (26.91 mmol) of KOH are added. Then 3.99 mL (26.91 mmol) of ethyl α-bromoisobutyrate are added slowly. The reaction is stirred for 18 h at room temperature under a nitrogen atmosphere. The reaction mixture is filtered, the solid is rinsed with ethanol and the filtrate is concentrated under reduced pressure. The crude material is purified by column chromatography (silica, eluent: n-heptanes, 0-20% ethyl acetate) to afford 2.68 g of ethyl 2-methyl-2-{[(2S)-oxan-2-ylmethyl]sulfanyl}propanoate (purity 90%). Yield: 72%; ES-MS: m/z 247 [M+H]; 1H NMR (500 MHz, CHLOROFORM-d) δ ppm 1.23-1.36 (5 H, m), 1.45-1.59 (8 H, m), 1.68 (1 H, d, J=13.12 Hz), 1.83 (1 H, d, J=10.99 Hz), 2.62-2.71 (1 H, m), 2.72-2.80 (1 H, m), 3.25-3.47 (2 H, m), 3.95-4.03 (1 H, m), 4.17 (2 H, q, J=7.12 Hz).

1. filtrationThe reaction mixture is filtered
2. washthe solid is rinsed with ethanol
3. concentrationthe filtrate is concentrated under reduced pressure
4. customThe crude material is purified by column chromatography (silica, eluent: n-heptanes, 0-20% ethyl acetate)

ORD record

ord-2d5a6468daac46619deaad240d1a9410

Source dataset

uspto-grants-2013_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08349871B2