Imidazole → Ethyl (S)-(-)-2-(tert-butyldimethylsilyloxy)propionate

HRID 78995

反応式

HRID 78995 の反応式
[C:1]([O:6][CH2:7][CH3:8])(=[O:5])[C@H:2]([CH3:4])[OH:3].N1C=CN=C1.[CH3:14][C:15]([Si:18](Cl)([CH3:20])[CH3:19])([CH3:17])[CH3:16]>C(Cl)Cl.O>[CH2:7]([O:6][C:1](=[O:5])[C@@H:2]([O:3][Si:18]([C:15]([CH3:17])([CH3:16])[CH3:14])([CH3:20])[CH3:19])[CH3:4])[CH3:8]

参加物

6

反応物 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 92831(L)-ethyl lactate

生成物 1

HCID 10966394Ethyl (S)-(-)-2-(tert-butyldimethylsilyloxy)propionate収率 100%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒

実験手順

To a solution of (S)-(−)-ethyl lactate (37.4 g, 0.32 mol) in DCM (200 mL) was added imidazole (25.75 g, 0.38 mol) and TBSCl (50 g, 0.33 mol). The reaction mixture was stirred at room temperature for 2 hours. The reaction was diluted with water and extracted with DCM (2×50 mL), the combined organic extracts washed with brine dried (MgSO4) and concentrated in vacuo to give the title product as a colourless oil (100%). 1H NMR (CDCl3, 400 MHz) 4.21 (1 H, q, J=6.73 Hz), 4.14-4.01 (2H, m), 1.29 (3H, d, J=6.79 Hz), 1.18 (3H, t, J=7.09 Hz), 0.80 (9H, s), −0.01 (6H, s).

後処理

  1. extractionextracted with DCM (2×50 mL)
  2. washthe combined organic extracts washed with brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-6a37e5b6d32240e9bdb28c03dcac8382
出典データセット
uspto-grants-2014_09
特許番号
US08841462B2

関連ノート

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