Imidazole → Ethyl 2-{[tert-butyl(dimethyl)silyl]oxy}hexanoate

HRID 1098072ノート

反応式

HRID 1098072 の反応式
N1C=CN=C1.[CH3:6][C:7]([Si:10](Cl)([CH3:12])[CH3:11])([CH3:9])[CH3:8].[CH2:14]([O:16][C:17](=[O:24])[CH:18]([OH:23])[CH2:19][CH2:20][CH2:21][CH3:22])[CH3:15].O>CN(C=O)C.C(OCC)C>[Si:10]([O:23][CH:18]([CH2:19][CH2:20][CH2:21][CH3:22])[C:17]([O:16][CH2:14][CH3:15])=[O:24])([C:7]([CH3:9])([CH3:8])[CH3:6])([CH3:12])[CH3:11]

参加物

7

反応物 4

HCID 795ImidazoleHCID 962WaterHCID 28928tert-Butyldimethylsilyl chlorideHCID 103589Hexanoic acid, 2-hydroxy-, ethyl ester

生成物 1

HCID 57438620Ethyl 2-{[tert-butyl(dimethyl)silyl]oxy}hexanoate収率 96.7%

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 6228Dimethylformamide溶媒

実験手順

Imidazole (4.10 g, 60.22 mmol) and TBDMSCl (3.60 g, 23.89 mmol) was added to a stirred solution of 2-hydroxy-hexanoic acid ethyl ester (3.20 g, 19.97 mmol) in DMF (25 mL). The reaction mixture was kept at ambient temperature for 18 hrs. Water and diethyl ether were added and the two phases were separated. The aqueous phase was extracted with diethyl ether. The organic extracts were combined and washed sequentially with 0.5 M HCl and water, dried over MgSO4 and concentrated in vacuo to give the title product (5.30 g), 1H NMR (300 MHz, CDCl3) δ 4.18 (m, 3H), 1.69 (m, 2H), 1.35 (m, 4H), 1.28 (t, 3H), 0.91 (m, 12H), 0.07 (d, 6H).

後処理

  1. customthe two phases were separated
  2. extractionThe aqueous phase was extracted with diethyl ether
  3. washwashed sequentially with 0.5 M HCl and water
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-2ac5d7dbb0bb42be8466d81fe25e496e
出典データセット
uspto-grants-2012_03
特許番号
US08143263B2

反応ノート

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