Propanoic acid, 2-bromo-2-methyl-, ethyl ester → 2-Methyl-2-(tetrahydro-pyran-4-ylsulfanyl)-propionic acid ethyl ester

HRID 538627노트

반응식

HRID 538627 반응식
[O:1]1[CH2:6][CH2:5][CH:4]([S:7]C(=O)C)[CH2:3][CH2:2]1.[OH-].[K+].Br[C:14]([CH3:21])([CH3:20])[C:15]([O:17][CH2:18][CH3:19])=[O:16]>CCO>[CH2:18]([O:17][C:15](=[O:16])[C:14]([CH3:21])([S:7][CH:4]1[CH2:5][CH2:6][O:1][CH2:2][CH2:3]1)[CH3:20])[CH3:19]

참가 물질

5

반응물 3

HCID 11745Propanoic acid, 2-bromo-2-methyl-, ethyl esterHCID 14797Potassium HydroxideHCID 18533108S-Tetrahydro-2H-pyran-4-YL ethanethioate

생성물 1

HCID 597039552-Methyl-2-(tetrahydro-pyran-4-ylsulfanyl)-propionic acid ethyl ester수율 71%

시약·촉매·용매 1

HCID 702Ethanol용매2회

반응 조건

온도
40 °C

실험 절차

A solution of 153 g (0.96 mol) of thioacetic acid S-(tetrahydro-pyran-4-yl) ester in EtOH (3.5 L) is degassed with nitrogen over 0.5 h and 125 g (2.23 mol) of KOH are added. Then a solution of 250 mL (1.68 mol) of ethyl α-bromoisobutyrate in EtOH (1 L) are added over 0.5 h, during which the temperature increased to 40° C. The reaction is stirred for 18 h at RT under a nitrogen atmosphere. The reaction mixture is filtered, the solid is washed with EtOH (0.5 L) and the filtrate is concentrated under reduced pressure. The crude material is dryloaded onto silica and purified by dry-flash column chromatography (silica, eluent: nheptanes, 2-10% EE) to afford 158 g of 2-methyl-2-(tetrahydro-pyran-4-ylsulfanyl)-propionic acid ethyl ester. Yield: 71%; ESI-MS: 233 [M+H]+

후처리

  1. filtrationThe reaction mixture is filtered
  2. washthe solid is washed with EtOH (0.5 L)
  3. concentrationthe filtrate is concentrated under reduced pressure
  4. custompurified by dry-flash column chromatography (silica, eluent: nheptanes, 2-10% EE)

출처 및 근거

ORD 기록
ord-03ba5336fd2d48d5ae590f54cfa3d1f4
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08865744B1

반응 노트

불러오는 중…