Tetrahydrofuran → trans-(2-(((Tert-butyldiphenylsilyl)oxy)methyl)cyclopropyl)methyl methanesulfonate

HRID 2202261ノート

反応式

HRID 2202261 の反応式
[Si:1]([O:18][CH2:19][C@@H:20]1[CH2:22][C@H:21]1[CH2:23][OH:24])([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:25][S:26](Cl)(=[O:28])=[O:27].C1COCC1>O>[CH3:25][S:26]([O:24][CH2:23][C@@H:21]1[CH2:22][C@H:20]1[CH2:19][O:18][Si:1]([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)(=[O:28])=[O:27]

参加物

5

反応物 3

HCID 8028TetrahydrofuranHCID 31297Methanesulfonyl chlorideHCID 10042906trans-(2-((Tert-butyldiphenylsilyloxy)methyl)cyclopropyl)methanol

生成物 1

HCID 10025044trans-(2-(((Tert-butyldiphenylsilyl)oxy)methyl)cyclopropyl)methyl methanesulfonate収率 100%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

TEA (0.450 mL, 3.23 mmol) was added to a mixture of trans-(2-((tert-butyldiphenylsilyloxy)methyl)cyclopropyl)methanol (1 g, 2.94 mmol), methanesulfonyl chloride (0.250 mL, 3.23 mmol) and THF (10 mL) at 0° C., and the mixture was stirred at room temperature for 2 hr. To the reaction mixture was added water, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, and dried over magnesium sulfate, and the solvent was evaporated under reduced pressure to give trans-(2-(((tert-butyldiphenylsilyl)oxy)methyl)cyclopropyl)methyl methanesulfonate (1.230 g, 2.94 mmol, 100%) as a colorless oil.

後処理

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure

出典と根拠

ORDレコード
ord-205e3c611ce84a34b53fb074622e9c7b
出典データセット
uspto-grants-2016_06
特許番号
US09365520B2

反応ノート

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