Sodium hydride → Ethyl 2-(4-n-Propylphenylthio)nonanoate

HRID 2257156

反応式

HRID 2257156 の反応式
[H-].[Na+].[CH2:3]([C:6]1[CH:11]=[CH:10][C:9]([SH:12])=[CH:8][CH:7]=1)[CH2:4][CH3:5].Br[CH:14]([CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[C:15]([O:17][CH2:18][CH3:19])=[O:16]>CN(C)C=O.C(OCC)(=O)C>[CH2:3]([C:6]1[CH:11]=[CH:10][C:9]([S:12][CH:14]([CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:8][CH:7]=1)[CH2:4][CH3:5]

参加物

6

反応物 3

HCID 24758Sodium hydrideHCID 110997Ethyl 2-bromononan-1-oateHCID 27604894-n-Propylthiophenol

生成物 1

HCID 14995384Ethyl 2-(4-n-Propylphenylthio)nonanoate収率 81%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

1.6 g (0.033 mole) sodium hydride (50% dispersion in mineral oil) was added to a solution of 5.0 g (0.033 mole) 4-propylthiophenol in 25 ml anhydrous dimethylformamide. After 15 minutes, 8.8 g (0.033 mole) ethyl 2-bromononanoate (prepared according to J. Labelled Compounds Radiopharm. 14, 713 (1978)) was added and the resulting mixture was stirred at room temperature overnight. The reaction mixture was then diluted with 150 ml ethyl acetate and the resulting mixture was washed with 5×60 ml water and then with 60 ml saturated aqueous sodium chloride solution. The ethyl acetate solution was dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The resulting oil was chromatographed on 600 g silica gel, eluting with 7:3 hexane/methylene chloride to yield 9.0 g (81% yield) of the desired product as an oil.

後処理

  1. washthe resulting mixture was washed with 5×60 ml water
  2. dry with materialThe ethyl acetate solution was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe resulting oil was chromatographed on 600 g silica gel
  6. washeluting with 7:3 hexane/methylene chloride

出典と根拠

ORDレコード
ord-31f0d2a051a84e43abbab7499aedfff6
出典データセット
uspto-grants-1997_08
特許番号
US05656634

関連ノート

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