Thionyl Chloride → 4-Chloro-2-butynyl 4-Cyano-3,4-diphenylbutyrate

HRID 851281

反応式

HRID 851281 の反応式
S(Cl)([Cl:3])=O.[C:5]([CH:7]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[CH:8]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH2:9][C:10]([O:12][CH2:13][C:14]#[C:15][CH2:16]O)=[O:11])#[N:6]>N1C=CC=CC=1.CCOCC.C(Cl)Cl>[C:5]([CH:7]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[CH:8]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH2:9][C:10]([O:12][CH2:13][C:14]#[C:15][CH2:16][Cl:3])=[O:11])#[N:6]

参加物

6

反応物 2

HCID 24386Thionyl ChlorideHCID 128348444-Hydroxy-2-butynyl 4-Cyano-3,4-diphenylbutyrate

生成物 1

HCID 128348464-Chloro-2-butynyl 4-Cyano-3,4-diphenylbutyrate収率 25%

試薬・触媒・溶媒 3

HCID 1049Pyridine溶媒HCID 3283Diethyl Ether溶媒HCID 6344Dichloromethane溶媒

実験手順

Thionyl chloride (3.56 g, 30.0 mmol) was added via syringe over a 5 min period to a stirred solution of 8.00 g (24.0 mmol) of 4-hydroxy-2-butynyl 4-cyano-3,4-diphenylbutyrate in 2.4 ml of pyridine at 0°. The reaction mixture was stirred at room temperature for 2 hours in a flask equipped with a Drierite tube. The mixture was diluted with 40 ml of ether and 100 ml of methylene chloride and was washed sequentially with 40 ml of hydrochloric acid, 40 ml of saturated aqueous sodium bicarbonate, three 40-ml portions of water and 40 ml of saturated aqueous sodium chloride. The organic phase was dried (MgSO4), filtered, stripped and purified by column chromatography on silica gel (hexanes/methylene chloride) to yield 2.11 g (25%) of the title compound. The infrared and nmr spectra are in accord with the assigned structure.

後処理

  1. customequipped with a Drierite tube
  2. washwas washed sequentially with 40 ml of hydrochloric acid, 40 ml of saturated aqueous sodium bicarbonate, three 40-ml portions of water and 40 ml of saturated aqueous sodium chloride
  3. dry with materialThe organic phase was dried (MgSO4)
  4. filtrationfiltered
  5. custompurified by column chromatography on silica gel (hexanes/methylene chloride)

出典と根拠

ORDレコード
ord-346b86d6f1914d2891dbb4436ce2d268
出典データセット
uspto-grants-1983_05
特許番号
US04383848

関連ノート

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