Triethylamine → (2R)-2-methoxypropyl 4-methylbenzene-1-sulfonate

HRID 339088ノート

反応式

HRID 339088 の反応式
[CH3:1][O:2][C@H:3]([CH3:6])[CH2:4][OH:5].[CH3:7]CN(CC)CC.[C:14]1(C)[C:15]([S:20](Cl)(=[O:22])=[O:21])=[CH:16][CH:17]=[CH:18][CH:19]=1>C(Cl)Cl>[CH3:7][C:18]1[CH:19]=[CH:14][C:15]([S:20]([O:5][CH2:4][C@H:3]([O:2][CH3:1])[CH3:6])(=[O:21])=[O:22])=[CH:16][CH:17]=1

参加物

5

反応物 3

HCID 8471TriethylamineHCID 8623o-Toluenesulfonyl chlorideHCID 27335882-Methoxy-1-propanol, (2R)-

生成物 1

HCID 13896527(2R)-2-methoxypropyl 4-methylbenzene-1-sulfonate収率 55.2%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒3 回

実験手順

To a stirred solution of crude (R)-2-methoxypropan-1-ol (4.30 g, 47.7 mmol) in DCM (200 mL) was added Et3N (10.0 mL, 71.6 mmol). A solution of toluene sulfonyl chloride (10.9 g, 57.3 mmol) in DCM (80 mL) was added dropwise at 0° C. under nitrogen. The reaction mixture was allowed to warm to ambient temperature and stirred overnight. The reaction was diluted with DCM, washed with saturated aqueous NaHCO3 solution and brine, dried and concentrated. The residue was purified by flash chromatography on silica gel (hexanes:EtOAc, 10:1 to 4:1) to give (R)-2-methoxypropyl 4-methylbenzenesulfonate (6.43 g, 55% for three steps).

後処理

  1. washwashed with saturated aqueous NaHCO3 solution and brine
  2. customdried
  3. concentrationconcentrated
  4. customThe residue was purified by flash chromatography on silica gel (hexanes:EtOAc, 10:1 to 4:1)

出典と根拠

ORDレコード
ord-8da25985801e481ab8f216b901773cd4
出典データセット
uspto-grants-2014_11
特許番号
US08889704B2

反応ノート

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