4-Toluenesulfonyl chloride → HCID 86601716, 화합물

HRID 880515

반응식

HRID 880515 반응식
C(N(CC)CC)C.[CH3:8][O:9][CH2:10][CH2:11][CH2:12][CH2:13][OH:14].[C:15]1([CH3:25])[CH:20]=[CH:19][C:18]([S:21](Cl)(=[O:23])=[O:22])=[CH:17][CH:16]=1>ClCCl>[CH3:8][O:9][CH2:10][CH2:11][CH2:12][CH2:13][O:14][S:21]([C:18]1[CH:19]=[CH:20][C:15]([CH3:25])=[CH:16][CH:17]=1)(=[O:23])=[O:22]

참가 물질

5

반응물 3

HCID 73974-Toluenesulfonyl chlorideHCID 81071-Butanol, 4-methoxy-HCID 8471Triethylamine

생성물 1

HCID 86601716HCID 86601716, 화합물수율 32.2%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Triethylamine (2.91 g, 28.86 mmol) was added to the stirred solution of 4-methoxy-1-butanol (1.00 g, 9.62 mmol) in dichloromethane (15 mL) at 0° C. and stirred for 15 min. p-Toluene sulfonyl chloride (1.83 g, 9.62 mmol) was added and the mixture was warmed to ambient temperature and stirred for 2 h. The reaction mixture was quenched with ice-water and the organic layer was separated. The aqueous layer was extracted with dichloromethane (3×5 mL) and the combined organic layers were washed with saturated sodium bicarbonate, water, and brine; dried over anhydrous sodium sulphate and concentrated in vacuo. The crude product was purified by column chromatography over silica gel (60-120 mesh) with 0% to 20% ethyl acetate in petroleum ether as eluent to afford 4-methoxybutyl-4-methylbenzenesulfonate (800 mg, 32%) as a liquid.

후처리

  1. additionwas added
  2. customThe reaction mixture was quenched with ice-water
  3. customthe organic layer was separated
  4. extractionThe aqueous layer was extracted with dichloromethane (3×5 mL)
  5. washthe combined organic layers were washed with saturated sodium bicarbonate, water, and brine
  6. dry with materialdried over anhydrous sodium sulphate
  7. concentrationconcentrated in vacuo
  8. customThe crude product was purified by column chromatography over silica gel (60-120 mesh) with 0% to 20% ethyl acetate in petroleum ether as eluent

출처 및 근거

ORD 기록
ord-e4ea53b126a146a2bc139d5c7719defe
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08993574B2

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