4-Methylbenzoyl Chloride → N-p-toluoyl valinol

HRID 369928노트

반응식

HRID 369928 반응식
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

참가 물질

6

반응물 4

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

생성물 1

HCID 18346087N-p-toluoyl valinol수율 89.6%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

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온도
0 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-84f46f7b2859461abcf372f616543bf0
출처 데이터셋
uspto-grants-2000_10
특허 번호
US06140344

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