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Imidazole → Methyl 2-(benzyloxy)-5-((1R)-2-bromo-1-{[tert-butyl(dimethyl)silyl]oxy]ethyl)benzoate

HRID 1455725
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인쇄 미리보기

반응식

HRID 1455725 반응식
[CH2:1]([O:8][C:9]1[CH:18]=[CH:17][C:16]([C@@H:19]([OH:22])[CH2:20][Br:21])=[CH:15][C:10]=1[C:11]([O:13][CH3:14])=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CN=C1.[Si:28](Cl)([C:31]([CH3:34])([CH3:33])[CH3:32])([CH3:30])[CH3:29]>CN(C)C1C=CN=CC=1.CN(C)C=O>[CH2:1]([O:8][C:9]1[CH:18]=[CH:17][C:16]([C@@H:19]([O:22][Si:28]([C:31]([CH3:34])([CH3:33])[CH3:32])([CH3:30])[CH3:29])[CH2:20][Br:21])=[CH:15][C:10]=1[C:11]([O:13][CH3:14])=[O:12])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 11003029(R)-Methyl 2-(benzyloxy)-5-(2-bromo-1-hydroxyethyl)benzoate

생성물 1

HCID 57438683Methyl 2-(benzyloxy)-5-((1R)-2-bromo-1-{[tert-butyl(dimethyl)silyl]oxy]ethyl)benzoate수율 97.3%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매
HCID 6228
Dimethylformamide
용매

실험 절차

A solution of methyl 2-(benzyloxy)-5-[(1R)-2-bromo-1-hydroxyethyl]benzoate (Tett. Left. 1994, 35(50), 9375) (71.05 g, 195 mmol), imidazole (18.52 g, 272 mmol), tert-butyidimethylsilyl chloride (32.23 g, 214 mmol) and 4-dimethylaminopyridine (0.44 g, 3.6 mmol) in N,N-dimethylformamide (270 ml) was stirred at room temperature under a nitrogen atmosphere for 24 hours. The solvent was removed in vacuo and the residue partitioned between ethyl acetate (500 ml) and water (500 ml). The organic phase was separated and washed with 2N hydrochloric acid (2×500 ml), saturated aqueous sodium bicarbonate (2×500 ml) saturated sodium chloride (500 ml), dried (magnesium sulfate) and the solvent removed in vacuo to give the title compound as a colourless oil (91.0 g).

후처리

  1. customThe solvent was removed in vacuo
  2. customthe residue partitioned between ethyl acetate (500 ml) and water (500 ml)
  3. customThe organic phase was separated
  4. washwashed with 2N hydrochloric acid (2×500 ml), saturated aqueous sodium bicarbonate (2×500 ml) saturated sodium chloride (500 ml)
  5. dry with materialdried (magnesium sulfate)
  6. customthe solvent removed in vacuo

출처 및 근거

ORD 기록
ord-a02576e664364c24a3ccf4d9c5f3b39f
출처 데이터셋
uspto-grants-2009_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07482487B2

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