Acetone Cyanohydrin → HCID 18978014、化合物

HRID 2392997ノート

反応式

HRID 2392997 の反応式
C(N(CC)CC)C.[CH3:8][C:9]([CH3:16])([CH3:15])[C:10](=[O:14])[CH2:11][C:12]#[N:13].[Cl:17][C:18]1[CH:26]=[C:25]([S:27][CH3:28])[CH:24]=[CH:23][C:19]=1[C:20](Cl)=[O:21].CC(C)(O)C#N>ClCCl>[Cl:17][C:18]1[CH:26]=[C:25]([S:27][CH3:28])[CH:24]=[CH:23][C:19]=1[C:20](=[O:21])[CH:11]([C:12]#[N:13])[C:10](=[O:14])[C:9]([CH3:16])([CH3:15])[CH3:8]

参加物

6

反応物 4

HCID 6406Acetone CyanohydrinHCID 8471TriethylamineHCID 108871Pentanenitrile, 4,4-dimethyl-3-oxo-HCID 189779562-Chloro-4-methylsulphenylbenzoyl chloride

生成物 1

HCID 18978014HCID 18978014、化合物収率 3.8%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

Triethylamine (1.78 g) was added to a stirred solution of 4,4-dimethyl-3-oxopentanenitrile (2.0 g) in dichloromethane and the mixture was stirred at room temperature for 2 hours. A solution of 2-chloro-4-methylsulphenylbenzoyl chloride (3.02 g) in dichloromethane was added and the mixture stirred at room temperature overnight. Acetone cyanohydrin (1.36 g) was added and the mixture stirred for 4 days, then filtered. The filtrate was washed with hydrochloric acid (2M), water, aqueous sodium bicarbonate solution, water, then dried (MgSO4) and filtered. The filtrate was evaporated to dryness and the residue purified by column chromatography (hexane, ethyl acetate and acetic acid). The main fraction was washed with aqueous sodium hydroxide (2M), water, dried and evaporated to dryness to give 1-(2-chloro-4-methylsulphenylphenyl)-2-cyano-4,4-dimethylpentan-1,3-dione (COMPOUND 664, 0.16 g) as a white solid, m.p. 97°-99° C.

後処理

  1. stirringthe mixture stirred at room temperature overnight
  2. stirringthe mixture stirred for 4 days
  3. filtrationfiltered
  4. washThe filtrate was washed with hydrochloric acid (2M), water, aqueous sodium bicarbonate solution, water
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customThe filtrate was evaporated to dryness
  8. customthe residue purified by column chromatography (hexane, ethyl acetate and acetic acid)
  9. washThe main fraction was washed with aqueous sodium hydroxide (2M), water
  10. customdried
  11. customevaporated to dryness

出典と根拠

ORDレコード
ord-7faebabe8e2746b7b38e665e217a8562
出典データセット
uspto-grants-1998_09
特許番号
US05804532

反応ノート

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