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

HRID 553595노트

반응식

HRID 553595 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]>C(O)C>[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 ethanol (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 is increased to 40° C. The reaction is stirred for 18 h at room temperature under a nitrogen atmosphere. The reaction mixture is filtered, the solid is washed with ethanol (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: n-heptanes, 2-10% ethyl acetate) to afford 158 g of 2-methyl-2-(tetrahydro-pyran-4-ylsulfanyl)-propionic acid ethyl ester as an orange-brown oil. Yield: 71%; ES-MS: m/z 233 [M+H]

후처리

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

출처 및 근거

ORD 기록
ord-17ff8094abbd4a95ae56354ce95e48cb
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08048899B2

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