Pyridine → [1-(Hydroxymethyl)-4-methylidenecyclohexyl]methyl 4-methylbenzenesulfonate

HRID 2040897ノート

反応式

HRID 2040897 の反応式
[OH:1][CH2:2][C:3]1([CH2:10][OH:11])[CH2:8][CH2:7][C:6](=[CH2:9])[CH2:5][CH2:4]1.N1C=CC=CC=1.[C:18]1([CH3:28])[CH:23]=[CH:22][C:21]([S:24](Cl)(=[O:26])=[O:25])=[CH:20][CH:19]=1>ClCCl>[CH3:28][C:18]1[CH:23]=[CH:22][C:21]([S:24]([O:1][CH2:2][C:3]2([CH2:10][OH:11])[CH2:8][CH2:7][C:6](=[CH2:9])[CH2:5][CH2:4]2)(=[O:26])=[O:25])=[CH:20][CH:19]=1

参加物

5

反応物 3

HCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 66603642[1-(Hydroxymethyl)-4-methylene-cyclohexyl]methanol

生成物 1

HCID 86662878[1-(Hydroxymethyl)-4-methylidenecyclohexyl]methyl 4-methylbenzenesulfonate

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

反応条件

温度
0 °C

実験手順

To a suspension of Compound 100b (0.25 g, 1.6 mmol) and pyridine (0.40 mL) in dichloromethane was added at 0° C. a solution of para-toluenesulphonyl chloride (0.336 g, 1.76 mmol) in 1 mL of dichloromethane. The reaction mixture was stirred at 0° C. for 30 min., then at r.t. for 3.5 h. Dilution with dichloromethane, washing with 1M aqueous NaHSO4 and brine, drying with Na2SO4, afforded, after evaporation, a crude which was purified by means of automated flash chromatography (SP01®TM-Biotage; gradient Dichloromethane-Methanol from 1:0 to 95:5) to give the title

後処理

  1. waitat r.t. for 3.5 h
  2. washDilution with dichloromethane, washing with 1M aqueous NaHSO4 and brine
  3. dry with materialdrying with Na2SO4
  4. customafforded
  5. customafter evaporation
  6. customa crude which was purified by means of automated flash chromatography (SP01®TM-Biotage; gradient Dichloromethane-Methanol from 1:0 to 95:5)
  7. customto give the title

出典と根拠

ORDレコード
ord-34873fa6358848f5b6204440f34f90c1
出典データセット
uspto-grants-2013_11
特許番号
US08580962B2

反応ノート

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