Imidazole → (Tert-butyl-dimethyl-silanyloxy)-cyclopropyl-acetic acid methyl ester

HRID 528488ノート

反応式

HRID 528488 の反応式
[CH3:1][O:2][C:3](=[O:9])[CH:4]([CH:6]1[CH2:8][CH2:7]1)[OH:5].[Si:10](Cl)([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:12])[CH3:11].N1C=CN=C1>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:9])[CH:4]([O:5][Si:10]([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:12])[CH3:11])[CH:6]1[CH2:8][CH2:7]1

参加物

5

反応物 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 11073449Methyl cyclopropyl(hydroxy)acetate

生成物 1

HCID 86711764(Tert-butyl-dimethyl-silanyloxy)-cyclopropyl-acetic acid methyl ester

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of cyclopropyl-hydroxy-acetic acid methyl ester (1.00 g, 7.68 mmol) in DCM (9 mL) was added tert-butyldimethylsilyl chloride (1.27 g, 8.45 mmol) and imidazole (628 mg, 9.22 mmol). The reaction mixture was stirred at RT for 65 hours before being quenched with water (10 mL) and 1M HCl (5 mL). The mixture was extracted with ethyl acetate (3×15 mL) and the combined organic phases were washed with 1M HCl (10 mL), brine (10 mL), dried (Na2SO4) then concentrated in vacuo. This gave (tert-Butyl-dimethyl-silanyloxy)-cyclopropyl-acetic acid methyl ester as an amber oil (1.66 g, 88%). 1H NMR (400 MHz, CDCl3): δ 3.81 (1H, d, J=6.33 Hz), 3.74 (3H, s), 1.23-1.13 (1H, m), 0.89 (9H, s), 0.52-0.0.38 (4H, m), 0.06 (3H, s), 0.04 (3H, s).

後処理

  1. custombefore being quenched with water (10 mL) and 1M HCl (5 mL)
  2. extractionThe mixture was extracted with ethyl acetate (3×15 mL)
  3. washthe combined organic phases were washed with 1M HCl (10 mL), brine (10 mL)
  4. dry with materialdried (Na2SO4)
  5. concentrationthen concentrated in vacuo

出典と根拠

ORDレコード
ord-aa50b66a045e434a8d9f13d1feb4dc36
出典データセット
uspto-grants-2016_05
特許番号
US09346817B2

反応ノート

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