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Imidazole → Methyl 4-((((1,1-dimethylethyl)(dimethyl)silyl)oxy)methyl)-2'-fluoro-5'-(methyloxy)-1,1'-biphenyl-2-carboxylate

HRID 1662529
Notes
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Reaction equation

HRID 1662529 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[C:10]1[C:11]([C:18]([O:20][CH3:21])=[O:19])=[CH:12][C:13]([CH2:16][OH:17])=[CH:14][CH:15]=1.[C:22]([Si:26]([CH3:29])([CH3:28])Cl)([CH3:25])([CH3:24])[CH3:23].N1C=CN=C1>CN(C=O)C>[CH3:23][C:22]([Si:26]([CH3:29])([CH3:28])[O:17][CH2:16][C:13]1[CH:12]=[C:11]([C:18]([O:20][CH3:21])=[O:19])[C:10]([C:3]2[CH:4]=[C:5]([O:8][CH3:9])[CH:6]=[CH:7][C:2]=2[F:1])=[CH:15][CH:14]=1)([CH3:25])[CH3:24]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 57705645Methyl 2'-fluoro-4-(hydroxymethyl)-5'-(methyloxy)-1,1'-biphenyl-2-carboxylate

Product 1

HCID 57706632Methyl 4-((((1,1-dimethylethyl)(dimethyl)silyl)oxy)methyl)-2'-fluoro-5'-(methyloxy)-1,1'-biphenyl-2-carboxylateYield 96%

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Conditions

Temperature
25 °C

Procedure

A 50 mL round bottom flask was charged with 66.13E (1.19 g, 4.1 mmol), tert-butyldimethylchlorosilane (commercially available from Aldrich) (0.68 g, 4.5 mmol), DMF (4 mL), and imidazole (0.70 g, 10 mmol). The mixture was stirred overnight at 25° C. and then diluted with hexanes. The organic phase was washed with 1 N HCl, water, and brine, dried (MgSO4), and concentrated to afford 83.18A (1.6 g, 96% yield) as a colorless oil. The product thus obtained was used without further purification.

Workup

  1. washThe organic phase was washed with 1 N HCl, water, and brine
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-462eab21371249bba6f0a7f5f5e7bcfa
Source dataset
uspto-grants-2011_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08030354B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes