tert-Butyldimethylsilyl chloride → (2R)-1-{[(1,1-Dimethylethyl)(dimethyl)silyl]oxy}propan-2-ol

HRID 20493

反応式

HRID 20493 の反応式
[Si:1](Cl)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[CH2:9]([OH:13])[C@H:10]([OH:12])[CH3:11].C(N(C(C)C)CC)(C)C>C(Cl)Cl.C(OCC)C.O>[Si:1]([O:13][CH2:9][C@H:10]([OH:12])[CH3:11])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

参加物

7

反応物 3

HCID 28928tert-Butyldimethylsilyl chlorideHCID 81531DiisopropylethylamineHCID 259994R-(-)-1,2-Propanediol

生成物 1

HCID 13175135(2R)-1-{[(1,1-Dimethylethyl)(dimethyl)silyl]oxy}propan-2-ol収率 80%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 3283Diethyl Ether溶媒HCID 6344Dichloromethane溶媒

実験手順

tert-Butyl(dimethyl)silyl chloride (5.90 g, 39-5 mmol) was added to a solution of (2R)-propane-1,2-diol (3.00 g, 39.5 mmol) in DCM (100 mL) followed by diisopropylethylamine (7.10 g, 55.3 mmol) and the reaction was stirred under argon for 72 h. The reaction was diluted with diethyl ether (500 mL) and water (140 mL) and the organic layer was separated then dried (MgSO4), filtered and evaporated. Purification by column chromatography, eluting with 1:15 to 1:10 ethyl acetate:hexane, afforded the title compound as a colourless oil (6.00 g, 80%).

後処理

  1. customthe organic layer was separated
  2. dry with materialthen dried (MgSO4)
  3. filtrationfiltered
  4. customevaporated
  5. customPurification by column chromatography
  6. washeluting with 1:15 to 1:10 ethyl acetate

出典と根拠

ORDレコード
ord-928e514db4e94bc4bc89503262906d42
出典データセット
uspto-grants-2010_06
特許番号
US07745475B2

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