Ethyl 3-mercaptopropionate → Ethyl 3-((4-hydroxyphenyl)-methylthio)propionate

HRID 450862

反応式

HRID 450862 の反応式
[H-].[Na+].[SH:3][CH2:4][CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7].[H][H].[OH:13][C:14]1[CH:21]=[CH:20][C:17]([CH2:18]Br)=[CH:16][CH:15]=1>CN(C=O)C>[OH:13][C:14]1[CH:21]=[CH:20][C:17]([CH2:18][S:3][CH2:4][CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:16][CH:15]=1

参加物

6

反応物 4

HCID 21625Ethyl 3-mercaptopropionateHCID 24758Sodium hydrideHCID 41663BromocresolHCID 178418361HCID 178418361、化合物

生成物 1

HCID 21964457Ethyl 3-((4-hydroxyphenyl)-methylthio)propionate

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of NaH (60% dispersed in oil, 0.731 g, 21.7 mmol) in dry DMF (15 ml) was added Ethyl 3-mercaptopropionate (2.66 g, 19.8 mmol). When the evolution of hydrogen ceased, 4-Hydroxybenzyl bromide from Step A was added. The reaction mixture was stirred for 16 hours at room temperature, quenched with sat. NH4Cl and concentrated in vacuo. The crude residue was taken in EtOAc and washed with water and brine. The aqueous layer was washed one more time with EtOAc. The combined organic layers were dried over Na2SO4, filtered and concentrated. The purification was done by flash chromatography on silica gel column (dichloromethane:ethyl acetate, 95:5) to provide the title compound.

後処理

  1. customquenched with sat. NH4Cl
  2. concentrationconcentrated in vacuo
  3. washwashed with water and brine
  4. washThe aqueous layer was washed one more time with EtOAc
  5. dry with materialThe combined organic layers were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe purification

出典と根拠

ORDレコード
ord-2d581205645746cfa8688cb97c6319ca
出典データセット
uspto-grants-2013_07
特許番号
US08487000B2

関連ノート

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