Diethyl Ether → 2-Fluoro-4-[1-hydroxy-1-(3-methyl-3H-imidazol-4-yl)-ethyl]-benzonitrile

HRID 1594883Notes

Reaction equation

HRID 1594883 reaction equation
[F:1][C:2]1[CH:9]=[C:8]([C:10]([C:12]2[N:13]([CH3:17])[CH:14]=[N:15][CH:16]=2)=[O:11])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].C[Mg+].[Br-].[CH2:21](OCC)C>C1COCC1>[F:1][C:2]1[CH:9]=[C:8]([C:10]([OH:11])([C:12]2[N:13]([CH3:17])[CH:14]=[N:15][CH:16]=2)[CH3:21])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 185332052-Fluoro-4-(3-methyl-3H-imidazole-4-carbonyl)-benzonitrileHCID 178418689HCID 178418689, compound

Product 1

HCID 216969592-Fluoro-4-[1-hydroxy-1-(3-methyl-3H-imidazol-4-yl)-ethyl]-benzonitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-Fluoro-4-(3-methyl-3H-imidazole-4-carbonyl)-benzonitrile (as described above in Step C) (0.603 g, 2.63 mmol) was dissolved in anhydrous THF (30 mL). A solution of 3.0M MeMgBr in diethyl ether (2.55 mL, 7.65 mmol) was added and stirred for 15 min. The reaction was quenched with NH4Cl solution, diluted with CH2Cl2 and saturated NaHCO3 solution and seperated. The aqueous layer was back extracted with CH2Cl2 (3×), the combined organic layers dried (MgSO4) and concentrated to give the title compound.

Workup

  1. customThe reaction was quenched with NH4Cl solution
  2. additiondiluted with CH2Cl2 and saturated NaHCO3 solution
  3. customseperated
  4. extractionThe aqueous layer was back extracted with CH2Cl2 (3×)
  5. dry with materialthe combined organic layers dried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-ee0cb24928004937a3f389fdaa676bde
Source dataset
uspto-grants-2001_09
Patent number
US06284755B1

Reaction notes

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