Pyridine → (5-Oxotetrahydrofuran-2-yl)methyl 4-methylbenzenesulfonate

HRID 481719

反応式

HRID 481719 の反応式
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7](Cl)(=[O:9])=[O:8])=[CH:3][CH:2]=1.[OH:12][CH2:13][CH:14]1[O:18][C:17](=[O:19])[CH2:16][CH2:15]1.N1C=CC=CC=1>C(Cl)Cl>[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7]([O:12][CH2:13][CH:14]2[O:18][C:17](=[O:19])[CH2:16][CH2:15]2)(=[O:9])=[O:8])=[CH:3][CH:2]=1

参加物

5

反応物 3

HCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 984315-(Hydroxymethyl)oxolan-2-one

生成物 1

HCID 4609541(5-Oxotetrahydrofuran-2-yl)methyl 4-methylbenzenesulfonate収率 76.1%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

p-Toluenesulfonyl chloride (23.65 g, 124.03 mmol) was added portion wise to a solution of (±)-dihydro-5-hydroxymethyl-2(3H)-furanone (example 56) (11.07 g, 95.43 mmol) and pyridine (15.4 mL, 190.86 mmol) in methylene chloride (300 mL) at 0° C. The solution was allowed to warm to rt and stirred overnight. The solution was then washed with water (2×100 mL), 0.5 n HCl until the washings were acidic and finally with saturated NaHCO3. After drying and concentrating, the residue was triturated with toluene to give the title compound as a white solid (19.63 g, 76%).

後処理

  1. washThe solution was then washed with water (2×100 mL), 0.5 n HCl until the washings
  2. customAfter drying
  3. concentrationconcentrating
  4. customthe residue was triturated with toluene

出典と根拠

ORDレコード
ord-9ecf2e7675374cd88f97532e780df932
出典データセット
uspto-grants-1998_08
特許番号
US05789394

関連ノート

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