Sodium hydride → Ethyl 7-acetyl-7-(p-toluoylamino)heptanoate

HRID 1796397노트

반응식

HRID 1796397 반응식
[H-].[Na+].[C:3]1([CH3:16])[CH:8]=[CH:7][C:6]([C:9]([NH:11][CH2:12][C:13](=[O:15])[CH3:14])=[O:10])=[CH:5][CH:4]=1.I[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24]>CN(C)C=O>[C:13]([CH:12]([NH:11][C:9]([C:6]1[CH:5]=[CH:4][C:3]([CH3:16])=[CH:8][CH:7]=1)=[O:10])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])(=[O:15])[CH3:14]

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 10880140Ethyl 6-iodohexanoateHCID 218667451-(p-Toluoylamino)-2-propanone

생성물 1

HCID 21866896Ethyl 7-acetyl-7-(p-toluoylamino)heptanoate수율 65.6%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매3회

실험 절차

A suspension (100 ml) of 60% sodium hydride (2.64 g) in N,N-dimethylformamide was cooled to −18° C. with an ice-sodium chloride bath, and 31 ml of a solution of 12.62 g of 1-(p-toluoylamino)-2-propanone in N,N-dimethylformamide was added dropwise slowly. After 1-hour-stirring, 31 ml of a solution of 16.21 g of ethyl 6-iodohexanoate in N,N-dimethylformamide was added dropwise slowly. The ice-bath was removed and the mixture was stirred for 18 hours at room temperature. After addition of ice-cold water, the reaction solution was extracted with ethyl acetate, washed with water and brine sequentially, dried over anhydrous magnesium sulfate and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (Wakogel® C-200, n-hexane:ethyl acetate=3:1) to provide 13.13 g of the objective compound as yellow oil.

후처리

  1. customThe ice-bath was removed
  2. stirringthe mixture was stirred for 18 hours at room temperature
  3. additionAfter addition of ice-cold water
  4. extractionthe reaction solution was extracted with ethyl acetate
  5. washwashed with water and brine sequentially
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationthe solvent was distilled off under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (Wakogel® C-200, n-hexane:ethyl acetate=3:1)

출처 및 근거

ORD 기록
ord-a4d0ccd7d9e445319c09ab2a0d27be5a
출처 데이터셋
uspto-grants-2006_04
특허 번호
US07030143B2

반응 노트

불러오는 중…