Imidazole → HCID 68453915, compound

HRID 2357546Notes

Reaction equation

HRID 2357546 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][OH:9])=[C:4]([F:10])[CH:3]=1.N1C=CN=C1.[C:16]([Si:20](Cl)([CH3:22])[CH3:21])([CH3:19])([CH3:18])[CH3:17]>C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][O:9][Si:20]([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:22])[CH3:21])=[C:4]([F:10])[CH:3]=1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 2773609(4-Chloro-2-fluorophenyl)methanol

Product 1

HCID 68453915HCID 68453915, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of (4-chloro-2-fluorophenyl)methanol (4.60 g, 28.6 mmol) in THF (100 mL) was added 1H-imidazole (1.95 g, 28.6 mmol) and tert-butylchlorodimethylsilane (4.32 g, 28.6 mmol) at room temperature. The reaction mixture was stirred for 12 h at RT. The white precipitate was filtered and the filtrate was washed with 0.1 N aqueous HCl. The separated aqueous phase was extracted with diethyl ether (2×40 mL). The combined organic phases were washed with saturated aqueous solution of sodium bicarbonate, and brine. The resulting organic solution was dried over magnesium sulfate and concentrated under reduced pressure. Flash chromatography on silica (hexanes) gave (4-chloro-2-fluorobenzyloxy)(tert-butyl)dimethylsilane as colorless oil. 1H NMR (300 MHz, CHLOROFORM-d) 6 ppm 7.31 (1H, t, J=8.1 Hz), 7.01 (1H, d, J=8.3 Hz), 6.91 (1 H, dd, J=9.9, 1.8 Hz), 4.64 (2H, s), 0.73-0.86 (9H, m), −0.06 (6H, s)

Workup

  1. filtrationThe white precipitate was filtered
  2. washthe filtrate was washed with 0.1 N aqueous HCl
  3. extractionThe separated aqueous phase was extracted with diethyl ether (2×40 mL)
  4. washThe combined organic phases were washed with saturated aqueous solution of sodium bicarbonate, and brine
  5. dry with materialThe resulting organic solution was dried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7068143e7ce747cc80ae64f15f0ef8a7
Source dataset
uspto-grants-2010_07
Patent number
US07759337B2

Reaction notes

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