Imidazole → HCID 131727842, compound

HRID 2355580Notes

Reaction equation

HRID 2355580 reaction equation
[C:1]([SiH2:5][O:6][C:7]([CH3:17])([CH3:16])[C:8]1[CH:9]=[CH:10][C:11]([F:15])=[C:12]([OH:14])[CH:13]=1)([CH3:4])([CH3:3])[CH3:2].N1C=CN=C1.[C:23]([Si:27](Cl)([CH3:29])[CH3:28])([CH3:26])([CH3:25])[CH3:24]>CN(C=O)C>[C:23]([Si:27]([CH3:29])([CH3:28])[O:14][C:12]1[CH:13]=[C:8]([C:7]([CH3:17])([CH3:16])[O:6][SiH2:5][C:1]([CH3:4])([CH3:2])[CH3:3])[CH:9]=[CH:10][C:11]=1[F:15])([CH3:26])([CH3:25])[CH3:24]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 137329300HCID 137329300, compound

Product 1

HCID 131727842HCID 131727842, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-(tert-butyl-dimethyl-silanyloxymethyl)-2-fluoro-phenol (4.60 g, 17.9 mmol, 1.0 equiv) in anhydrous DMF (20 mL) at 0° C. under Ar was added imidazole (1.34 g, 19.7 mmol, 1.1 equiv) and tert-butyl-chloro-dimethyl-silane (2.97 g, 19.7 mmol, 1.1 equiv). After the addition was completed the cooling bath was removed and the reaction stirred for 18 h at rt. The reaction mixture was poured on ice, extracted with ethyl acetate (2×100 mL) and the combined organic phases washed with a sat. solution of Na2CO3 (2×100 mL) and NaCl (2×100 mL). The organic phase was dried over Na2SO4 and concentrated by evaporation under reduced pressure yielding 4.50 g (68%) of the title compound. 1H NMR (400 MHz, CDCl3): δ0.00 (s, 6H), 0.10 (s, 6H), 0.85 (s, 9H), 0.92 (s, 9H), 4.55 (s, 2H), 6.71-6.74 (m, 1H), 6.80-6.83 (m, 1H), 6.87-6.92 (m, 1H). MS (EI): 370.2 [M]+.

Workup

  1. additionAfter the addition
  2. customwas removed
  3. additionThe reaction mixture was poured on ice
  4. extractionextracted with ethyl acetate (2×100 mL)
  5. washthe combined organic phases washed with a sat. solution of Na2CO3 (2×100 mL) and NaCl (2×100 mL)
  6. dry with materialThe organic phase was dried over Na2SO4
  7. concentrationconcentrated by evaporation under reduced pressure

Sources & evidence

ORD record
ord-ac454c077c5942e08499fb6441f99b10
Source dataset
uspto-grants-2010_07
Patent number
US07754744B2

Reaction notes

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