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

HRID 379068Notes

Reaction equation

HRID 379068 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 (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-2f279e0800d9483cbacc09df09c2e548
Source dataset
uspto-grants-2001_10
Patent number
US06297239B1

Reaction notes

Loading…