Imidazole → ((4-Bromo-2-methoxybenzyl)oxy)(tert-butyl)dimethylsilane

HRID 1505922노트

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HRID 1505922 반응식
[Si:1](Cl)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[Br:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][OH:17])=[C:12]([O:18][CH3:19])[CH:11]=1.N1C=CN=C1>CN(C=O)C>[Br:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][O:17][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2])=[C:12]([O:18][CH3:19])[CH:11]=1

참가 물질

5

반응물 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 151282434-Bromo-2-methoxybenzyl alcohol

생성물 1

HCID 18687376((4-Bromo-2-methoxybenzyl)oxy)(tert-butyl)dimethylsilane수율 98%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

tert-Butyldimethylsilyl chloride (1.04 g, 6.9 mmol) was added to a mixture of (4-bromo-2-methoxyphenyl)methanol (1.0 g, 4.6 mol) and imidazole (470 mg, 7.0 mmol) in DMF (15 mL) and the resultant mixture was stirred at ambient temperature for 66 h. The mixture was concentrated to about a third of the original volume then diluted with water and extracted with diethyl ether (×3). The combined organic layer was dried over magnesium sulfate, filtered and evaporated. The resultant residue was purified by chromatography (silica, 50 g column, Si-SPE, 5% diethyl ether in pentane) to afford the title compound as a colourless oil (1.51 g, 98%). 1H NMR (CDCl3, 400 MHz): 7.34 (dt, J=8.1, 1.05 Hz, 1H); 7.11 (dd, J=8.1, 1.8 Hz, 1H); 6.95 (d, J=1.8 Hz, 1H); 4.69 (d, J=1.0 Hz, 2H); 3.81 (s, 3H); 0.97-0.94 (m, 9H); 0.13-0.08 (m, 6H).

후처리

  1. concentrationThe mixture was concentrated to about a third of the original volume
  2. additionthen diluted with water
  3. extractionextracted with diethyl ether (×3)
  4. dry with materialThe combined organic layer was dried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe resultant residue was purified by chromatography (silica, 50 g column, Si-SPE, 5% diethyl ether in pentane)

출처 및 근거

ORD 기록
ord-4e01df542c7b4b539718e00a446f12b4
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09216980B2

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