Imidazole → tert-Butyl(5-ethyl-2-fluorophenoxy)dimethylsilane

HRID 1438156Notes

Reaction equation

HRID 1438156 reaction equation
[CH2:1]([C:3]1[CH:4]=[CH:5][C:6]([F:10])=[C:7]([OH:9])[CH:8]=1)[CH3:2].[Si:11](Cl)([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12].N1C=CN=C1>CN(C=O)C>[C:14]([Si:11]([O:9][C:7]1[CH:8]=[C:3]([CH2:1][CH3:2])[CH:4]=[CH:5][C:6]=1[F:10])([CH3:13])[CH3:12])([CH3:17])([CH3:16])[CH3:15]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 187116495-Ethyl-2-fluorophenol

Product 1

HCID 59838026tert-Butyl(5-ethyl-2-fluorophenoxy)dimethylsilaneYield 66%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 118A (3.75 g, 26.8 mmol) in DMF (20 mL) was added tert-butyldimethylsilyl chloride (6.1 g) and imidazole (2.6 g). The mixture was stirred at rt for overnight. It was then diluted with EtOAc/hexanes (1:4) and washed with water and brine. The organic extracts were dried and concentrated. The crude product was purified by column chromatography to give 118B (4.46 g, 66% yield) as an oil. 1H NMR (400 MHz, CDCl3) δ ppm 0.21 (none, 6H) 0.99 (s, 9H) 1.18 (t, J=7.69 Hz, 3H) 2.54 (q, J=7.76 Hz, 2H) 6.64-6.76 (m, 2H) 6.93 (dd, J=10.55, 8.35 Hz, 1H).

Workup

  1. washwashed with water and brine
  2. customThe organic extracts were dried
  3. concentrationconcentrated
  4. customThe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-59e265fa4a964486b549295f71080e7a
Source dataset
uspto-grants-2009_11
Patent number
US07622585B2

Reaction notes

Loading…