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

HRID 2040897노트

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HRID 2040897 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

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온도
0 °C

실험 절차

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

후처리

  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

출처 및 근거

ORD 기록
ord-34873fa6358848f5b6204440f34f90c1
출처 데이터셋
uspto-grants-2013_11
특허 번호
US08580962B2

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