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

HRID 538627ノート

反応式

HRID 538627 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒2 回

反応条件

温度
40 °C

実験手順

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]+

後処理

  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)

出典と根拠

ORDレコード
ord-03ba5336fd2d48d5ae590f54cfa3d1f4
出典データセット
uspto-grants-2014_10
特許番号
US08865744B1

反応ノート

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