Imidazole → Butanoic acid, 3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-, ethyl ester, (3R)-

HRID 382005ノート

反応式

HRID 382005 の反応式
[OH:1][C@H:2]([CH3:9])[CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5].[Si:10](Cl)([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:12])[CH3:11].N1C=CN=C1>CN(C=O)C>[O:1]([C@H:2]([CH3:9])[CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5])[Si:10]([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:12])[CH3:11]

参加物

5

反応物 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 440030ethyl (3R)-3-hydroxybutanoate

生成物 1

HCID 12914545Butanoic acid, 3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-, ethyl ester, (3R)-

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a stirred, room temperature solution of ethyl (R)-3-hydroxybutanoate (5.00 g, 37.8 mmol) and tert-butyldimethylsilyl chloride (6.85 g, 45.5 mmol) in DMF (90 mL) was added imidazole (3.87 g, 56.9 mmol). This reaction mixture was stirred at room temperature for 18 hours. The reaction mixture was partitioned between hexane (300 mL) and water (100 mL). The organic layer was washed with water (2×100 mL) then dried (MgSO4) and filtered. The filtrate was concentrated under reduced pressure to give the title compound.

後処理

  1. customThe reaction mixture was partitioned between hexane (300 mL) and water (100 mL)
  2. washThe organic layer was washed with water (2×100 mL)
  3. dry with materialthen dried (MgSO4)
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated under reduced pressure

出典と根拠

ORDレコード
ord-4e6d7e8ac07941c4b62e98f4091d403a
出典データセット
uspto-grants-2001_10
特許番号
US06307047B1

反応ノート

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