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

HRID 1098072노트

반응식

HRID 1098072 반응식
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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 6228Dimethylformamide용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-2ac5d7dbb0bb42be8466d81fe25e496e
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08143263B2

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