4-Methylbenzoyl Chloride → N-p-toluoyl valinol

HRID 369928ノート

反応式

HRID 369928 の反応式
C(N(C(C)C)CC)(C)C.[NH2:10][CH:11]([CH2:15][OH:16])[CH:12]([CH3:14])[CH3:13].[C:17]1([CH3:26])[CH:22]=[CH:21][C:20]([C:23](Cl)=[O:24])=[CH:19][CH:18]=1.[OH-].[Na+]>C(Cl)Cl>[C:17]1([CH3:26])[CH:22]=[CH:21][C:20]([C:23]([NH:10][C@H:11]([CH2:15][OH:16])[CH:12]([CH3:14])[CH3:13])=[O:24])=[CH:19][CH:18]=1

参加物

6

反応物 4

HCID 134054-Methylbenzoyl ChlorideHCID 14798Sodium HydroxideHCID 79019ValinolHCID 81531Diisopropylethylamine

生成物 1

HCID 18346087N-p-toluoyl valinol収率 89.6%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

反応条件

温度
0 °C

実験手順

Diisopropylethyl amine (17.4 mL, 134 mmol) was added a solution of (DL)-valinol (9.85 g, 95 mmol) in methylene chloride (100 ml). The reaction mixture was cooled to 0° C., treated with a solution of p-toluoyl chloride (12.8 mL, 91 mmol) in methylene chloride (50 mL) and then allowed to warm to room temperature. After stirring for 3 h, excess aqueous sodium hydroxide solution was added and the reaction was transferred to a separatory funnel. The organic layer was separated and the aqueous layer washed with one portion of methylene chloride. The combined organic layers were washed with water and brine, dried over magnesium sulfate and concentrated in vacuo. Chromatography eluting with 25% ethyl acetate in hexanes, followed by 50% ethyl acetate in hexanes gave N-p-toluoyl valinol (18.04 g).

後処理

  1. temperatureto warm to room temperature
  2. customthe reaction was transferred to a separatory funnel
  3. customThe organic layer was separated
  4. washthe aqueous layer washed with one portion of methylene chloride
  5. washThe combined organic layers were washed with water and brine
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated in vacuo
  8. washChromatography eluting with 25% ethyl acetate in hexanes

出典と根拠

ORDレコード
ord-84f46f7b2859461abcf372f616543bf0
出典データセット
uspto-grants-2000_10
特許番号
US06140344

反応ノート

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