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

HRID 890668ノート

反応式

HRID 890668 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒3 回

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-571d5c2090bc4214a9ac77abd0d5b466
出典データセット
uspto-grants-2006_02
特許番号
US06998412B2

反応ノート

読み込み中…