Water → (S)-tetrahydrofuran-3-yl methanesulfonate

HRID 874390ノート

反応式

HRID 874390 の反応式
[O:1]1[CH2:5][CH2:4][C@H:3]([OH:6])[CH2:2]1.C(N(CC)CC)C.[CH3:14][S:15](Cl)(=[O:17])=[O:16].O>C(Cl)Cl>[CH3:14][S:15]([O:6][C@H:3]1[CH2:4][CH2:5][O:1][CH2:2]1)(=[O:17])=[O:16]

参加物

6

反応物 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 2733227(S)-(+)-3-Hydroxytetrahydrofuran

生成物 1

HCID 57561588(S)-tetrahydrofuran-3-yl methanesulfonate収率 83.1%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

A solution of (S)-tetrahydrofuran-3-ol (1.0 g, 11 mmol) and triethylamine (9.4 mL, 86 mmol) in CH2Cl2 (20 mL) was cooled in an ice-water bath. To this, methanesulfonyl chloride (3.0 mL, 39 mmol) diluted in CH2Cl2 (10 mL) was added dropwise. The reaction was left stirring for 12 hours at room temperature. Water was added, and organic phases extracted in CH2Cl2 (3×50 mL), which were subsequently dried onto silica and purified by silica gel chromatography (50% EtOAc:Hexanes to 100% EtOAc gradient) to afford (S)-tetrahydrofuran-3-yl methanesulfonate (1.52 g, brown oil, 83% yield).

後処理

  1. additionwas added dropwise
  2. waitThe reaction was left
  3. extractionorganic phases extracted in CH2Cl2 (3×50 mL)
  4. customwhich were subsequently dried onto silica
  5. custompurified by silica gel chromatography (50% EtOAc:Hexanes to 100% EtOAc gradient)

出典と根拠

ORDレコード
ord-0f31010e524b41c087dbe5f4c7a1b242
出典データセット
uspto-grants-2015_03
特許番号
US08980899B2

反応ノート

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