Imidazole → tert-Butyl(3-(2-fluorophenyl)propoxy)dimethylsilane

HRID 471203Notes

Reaction equation

HRID 471203 reaction equation
[Si:1](Cl)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].N1C=CN=C1.[F:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[CH2:21][CH2:22][CH2:23][OH:24]>CN(C=O)C.C(OCC)(=O)C>[C:4]([Si:1]([O:24][CH2:23][CH2:22][CH2:21][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=1[F:14])([CH3:3])[CH3:2])([CH3:7])([CH3:6])[CH3:5]

Participants

6

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 126185173-(2-Fluorophenyl)propan-1-ol

Product 1

HCID 57989116tert-Butyl(3-(2-fluorophenyl)propoxy)dimethylsilane

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

tert-Butyldimethylsilyl chloride (3.19 g) was added to a solution of imidazole (3.6 g) and 3-(2-fluorophenyl)propan-1-ol (example 88, step a) (2.72 g) in dry DMF (30 mL) cooled in an ice bath. After 45 min, the reaction mixture was diluted with ethyl acetate (100 mL), washed with water (3×100 mL) and evaporated. The resulting gum was purified by silica gel chromatography eluting with isohexane. The fractions containing product were combined and evaporated to give the subtitled compound as a clear oil. Yield 4.4 g.

Workup

  1. temperaturecooled in an ice bath
  2. washwashed with water (3×100 mL)
  3. customevaporated
  4. customThe resulting gum was purified by silica gel chromatography
  5. washeluting with isohexane
  6. additionThe fractions containing product
  7. customevaporated

Sources & evidence

ORD record
ord-4cdee596ed684782abbec5ff149bb809
Source dataset
uspto-grants-2014_01
Patent number
US08629271B2

Reaction notes

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