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

HRID 1455725
Notes
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Reaction equation

HRID 1455725 reaction equation
[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
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 14284
4-(Dimethylamino)pyridine
Catalyst
HCID 6228DimethylformamideSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-a02576e664364c24a3ccf4d9c5f3b39f
Source dataset
uspto-grants-2009_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07482487B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes