4-Chlorobenzenesulfonyl chloride → HCID 54417527、化合物

HRID 1377383ノート

反応式

HRID 1377383 の反応式
[CH2:1]([OH:27])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26].C(N(CC)CC)C.[Cl:35][C:36]1[CH:41]=[CH:40][C:39]([S:42](Cl)(=[O:44])=[O:43])=[CH:38][CH:37]=1>C(Cl)Cl>[CH2:1]([O:27][S:42]([C:39]1[CH:40]=[CH:41][C:36]([Cl:35])=[CH:37][CH:38]=1)(=[O:44])=[O:43])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26]

参加物

5

反応物 3

HCID 73984-Chlorobenzenesulfonyl chlorideHCID 8471TriethylamineHCID 681711-Hexacosanol

生成物 1

HCID 54417527HCID 54417527、化合物収率 22%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

A solution of hexacosanol (250 mgs, 0.654 mmol), triethylamine (125 1, 0.900 mmol) and 4-chlorobenzenesulphonyl chloride (150 mgs, 0.711 mmol) in methylene chloride (30 ml) is stirred at room temperature for 120 h. The reaction mixture is then diluted with methylene chloride (20 ml) and washed with water (2×50 ml). The organic phase is dried over magnesium sulphate, filtered and concentrated to give a crude product. Flash column chromatography on silica gel (10:1 hexane:ethyl acetate) followed by recrystallization from methanol gives n-hexacosanyl-4-chlorobenzenesulphonate (80 mgs, 22%).

後処理

  1. washwashed with water (2×50 ml)
  2. dry with materialThe organic phase is dried over magnesium sulphate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto give a crude product
  6. customFlash column chromatography on silica gel (10:1 hexane:ethyl acetate) followed by recrystallization from methanol

出典と根拠

ORDレコード
ord-11081f1085fe46a4b1a54faa635e9b6f
出典データセット
uspto-grants-1997_09
特許番号
US05665328

反応ノート

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