Methanesulfonyl chloride → (R)-(tetrahydrofuran-2-yl)methyl methanesulfonate

HRID 1623420ノート

反応式

HRID 1623420 の反応式
[O:1]1[CH2:5][CH2:4][CH2:3][C@@H:2]1[CH2:6][OH:7].[CH3:8][S:9](Cl)(=[O:11])=[O:10]>C(Cl)Cl>[CH3:8][S:9]([O:7][CH2:6][C@H:2]1[CH2:3][CH2:4][CH2:5][O:1]1)(=[O:11])=[O:10]

参加物

4

反応物 2

HCID 31297Methanesulfonyl chlorideHCID 6931745(2R)-oxolan-2-ylmethanol

生成物 1

HCID 18649742(R)-(tetrahydrofuran-2-yl)methyl methanesulfonate収率 92.6%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A mixture of (R)-(tetrahydrofuran-2-yl)methanol (600 mg, 5.87 mmol), DCM (35 ml), TEA (0.983 ml, 7.05 mmol) was diluted with methanesulfonyl chloride (0.467 ml, 5.99 mmol), via a dropwise addition. The reaction mixture was stirred at ambient temperature for 5 hours and the reaction progress was followed by LCMS. The crude reaction mixture was washed with saturated sodium bicarbonate (1×), water (2×), filtered and concentrated to a constant mass, giving 980 mg of the title compound, which was used without further purification. LCMS (m/z): 181.0 (MH+), retention time=0.40 min

後処理

  1. customThe crude reaction mixture
  2. washwas washed with saturated sodium bicarbonate (1×), water (2×)
  3. filtrationfiltered
  4. concentrationconcentrated to a constant mass

出典と根拠

ORDレコード
ord-c226b04c762247c3b5a09bdb8ab657be
出典データセット
uspto-grants-2014_07
特許番号
US08778951B2

反応ノート

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