4-Toluenesulfonyl chloride → Tetrahydrofuran-3-YL 4-methylbenzenesulfonate, (3R)-

HRID 237453

反応式

HRID 237453 の反応式
[O:1]1[CH2:5][CH2:4][C@@H:3]([OH:6])[CH2:2]1.[C:7]1([CH3:17])[CH:12]=[CH:11][C:10]([S:13](Cl)(=[O:15])=[O:14])=[CH:9][CH:8]=1>ClCCl.N1C=CC=CC=1>[O:1]1[CH2:5][CH2:4][C@@H:3]([O:6][S:13]([C:10]2[CH:11]=[CH:12][C:7]([CH3:17])=[CH:8][CH:9]=2)(=[O:15])=[O:14])[CH2:2]1

参加物

5

反応物 2

HCID 73974-Toluenesulfonyl chlorideHCID 641512(-)-3-Hydroxytetrahydrofuran

生成物 1

HCID 11149197Tetrahydrofuran-3-YL 4-methylbenzenesulfonate, (3R)-

試薬・触媒・溶媒 2

HCID 1049Pyridine溶媒HCID 6344Dichloromethane溶媒2 回

実験手順

To a solution of (R)-tetrahydrofuran-3-ol (25.4 g) in dichloromethane (250 mL) and pyridine (60 mL) is added at 0° C. N,N-dimethylaminopyridine (DMAP; 1 g) and p-toluene-sulfonylchloride (73 g) in portions. The mixture is stirred for 12 hours at room temperature, diluted with dichloromethane and washed with 1 M aqueous HCl solution and brine. After drying (MgSO4) the solvent is evaporated and the residue is chromatographed on silica gel (dichloromethane/methanol 100:0→95:5) to give the title compound. Yield: 59.5 g; Mass spectrum (ESI+): m/z=243 [M+H]+.

後処理

  1. washwashed with 1 M aqueous HCl solution and brine
  2. dry with materialAfter drying (MgSO4) the solvent
  3. customis evaporated
  4. customthe residue is chromatographed on silica gel (dichloromethane/methanol 100:0→95:5)

出典と根拠

ORDレコード
ord-c0a99b9bb1964f56b30ad28a2897bf38
出典データセット
uspto-grants-2014_02
特許番号
US08642585B2

関連ノート

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