Sodium hydride → HCID 67092210, compound

HRID 2074110Notes

Reaction equation

HRID 2074110 reaction equation
[C:1]([N:20]1[CH:24]=[C:23]([C:25](=[O:27])[CH3:26])[N:22]=[CH:21]1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[F:30][C:31]1[CH:36]=[CH:35][C:34]([CH2:37][C:38](OC)=[O:39])=[CH:33][CH:32]=1>C1COCC1>[F:30][C:31]1[CH:36]=[CH:35][C:34]([CH2:37][C:38](=[O:39])[CH2:26][C:25]([C:23]2[N:22]=[CH:21][N:20]([C:1]([C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)([C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=3)[C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[CH:24]=2)=[O:27])=[CH:33][CH:32]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 2733233Methyl 2-(4-fluorophenyl)acetateHCID 104280901-(1-trityl-1H-imidazol-4-yl)ethanone

Product 1

HCID 67092210HCID 67092210, compoundYield 48.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-(1-trityl-1H-imidazol-4-yl)ethanone (1.5 g, 4.26 mmol) in anhydrous THF (25 mL) was added NaH (0.23 g, 8.52 mmol) at 0° C. The mixture was stirred at RT for 2 hours, and methyl (4-fluorophenyl)acetate (1.43 g, 12.78 mmol) was added at 0° C. The mixture was refluxed overnight. The mixture was evaporated and the residue was purified via column chromatography (silica gel, EtOAc/Petroleum ether 1:5) to yield the title compound (1.018 g, 48.0%) as colorless oil.

Workup

  1. temperatureThe mixture was refluxed overnight
  2. customThe mixture was evaporated
  3. customthe residue was purified via column chromatography (silica gel, EtOAc/Petroleum ether 1:5)

Sources & evidence

ORD record
ord-cf559c5228c74a28ad7b1ef80681bc9e
Source dataset
uspto-grants-2011_04
Patent number
US07919488B2

Reaction notes

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