4-Toluenesulfonyl chloride → HCID 86601716、化合物

HRID 880515

反応式

HRID 880515 の反応式
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]

参加物

5

反応物 3

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

生成物 1

HCID 86601716HCID 86601716、化合物収率 32.2%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-e4ea53b126a146a2bc139d5c7719defe
出典データセット
uspto-grants-2015_03
特許番号
US08993574B2

関連ノート

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