Imidazole → HCID 13732855, compound

HRID 1731806Notes

Reaction equation

HRID 1731806 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[C:11]1[CH:12]=[C:13]([CH:16]=[CH:17][CH:18]=1)[CH2:14][OH:15].N1C=CN=C1.[Si:24](Cl)([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:26])[CH3:25]>CN(C)C=O>[Si:24]([O:15][CH2:14][C:13]1[CH:12]=[C:11]([C:3]2[CH:4]=[C:5]([N+:8]([O-:10])=[O:9])[CH:6]=[CH:7][C:2]=2[F:1])[CH:18]=[CH:17][CH:16]=1)([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:26])[CH3:25]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 13732856HCID 13732856, compound

Product 1

HCID 13732855HCID 13732855, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 4.04 g 3-(2-fluoro-5-nitrophenyl)-benzyl alcohol, 2.23 g imidazole and 2.46 g t-butyldimethylsilylchloride in 100 ml N,N-dimethylformamide was stirred at room temperature for 30 minutes. The reaction mixture was then partitioned between water and ether. The combined organic extracts were washed three times with water, dried and evaporated yielding the product as a yellow oil (5.9 g, 99% yield) which was purified on silica gel to give a yellow solid of m.p. 44°-45° C. NMR (CDCl3, 250 MHz): 8.4 (dd, 1H), 8.34 (eight line multiplet, 1H), 7.5 (m, 4H), 7.3 (m, 1H), 4.83 (s, 2H), 0.95 (s, 9H), 0.15 (s, 6H).

Workup

  1. customThe reaction mixture was then partitioned between water and ether
  2. washThe combined organic extracts were washed three times with water
  3. customdried
  4. customevaporated

Sources & evidence

ORD record
ord-811fac6009fd42fda0516d8b33c30701
Source dataset
uspto-grants-1986_11
Patent number
US04623650

Reaction notes

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