Diethyl Ether → 4-Allyl-2-fluoro-1-triphenylmethylimidazole

HRID 1463170Notes

Reaction equation

HRID 1463170 reaction equation
[F:1][C:2]1[N:3]([C:7]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:4]=[CH:5][N:6]=1.[C:26]([Li])(C)([CH3:28])[CH3:27].C(Br)C=C.CCOCC>C1COCC1.CCCCC>[CH2:28]([C:5]1[N:6]=[C:2]([F:1])[N:3]([C:7]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:4]=1)[CH:26]=[CH2:27]

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 7841Allyl bromideHCID 204324542-Fluoro-1-trityl-1H-imidazoleHCID 178418306HCID 178418306, compound

Product 1

HCID 204323494-Allyl-2-fluoro-1-triphenylmethylimidazole

Reagents, catalysts & solvents 2

HCID 8003PentaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-fluoro-1-triphenylmethylimidazole (1.31 g.) in THF (22 ml.) at -70° under argon was added t-butyl lithium (4 ml. of a 2M solution in pentane). The red solution was stirred at -70° for 2 hours and then cuprous iodide (0.78 g.) added. The resulting dark red solution was stirred at -70° for 1 hour and then allyl bromide (1.8 ml.) added. The mixture was allowed to warm to ambient temperature over 18 hours and then poured into ether (150 ml.). The mixture was washed with saturated aqueous ammonium chloride (6×50 ml.), then brine (50 ml.), treated with charcoal and dried (MgSO4). The solution was evaporated to give 4-allyl-2-fluoro-1-triphenylmethylimidazole as a pale yellow solid, m.p. 136°-138°.

Workup

  1. stirringThe resulting dark red solution was stirred at -70° for 1 hour
  2. washThe mixture was washed with saturated aqueous ammonium chloride (6×50 ml.)
  3. additionbrine (50 ml.), treated with charcoal
  4. dry with materialdried (MgSO4)
  5. customThe solution was evaporated

Sources & evidence

ORD record
ord-15520ed2d97b4d26895dedba804c584d
Source dataset
uspto-grants-1984_07
Patent number
US04463173

Reaction notes

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