Pyridine, hydrofluoride (1:1) → HCID 178450081, compound

HRID 1368543Notes

Reaction equation

HRID 1368543 reaction equation
[Si]([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[CH:15]=[C:14]([C:19]([C:24]1[N:25]=[CH:26][NH:27][CH:28]=1)([OH:23])[CH:20]([CH3:22])[CH3:21])[CH:13]=[CH:12]2)(C(C)(C)C)(C)C.N1C=CC=CC=1.F.C(=O)([O-])O.[Na+]>C1COCC1>[OH:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[CH:15]=[C:14]([C:19]([C:24]1[N:25]=[CH:26][NH:27][CH:28]=1)([OH:23])[CH:20]([CH3:22])[CH3:21])[CH:13]=[CH:12]2

Participants

5

Reactant 3

HCID 64774Pyridine, hydrofluoride (1:1)HCID 516892Sodium BicarbonateHCID 178450086HCID 178450086, compound

Product 1

HCID 178450081HCID 178450081, compoundYield 75.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-(6-tert-butyldimethylsilyloxynaphthalen-2-yl -1-(1H-imidazol-4-yl)-2-methylpropanol (1.60 g) in THF (10 mL) was added 70% aqueous solution of hydrogen fluoride-pyridine (3 ml) under ice cooling. The mixture was stirred for 30 min under ice cooling and for 2 h at room temperature. The mixture was neutralized with saturated solution of sodium hydrogencarbonate, extracted with dichloromethane and dried. The solvent was distilled off and the residue was purified by column chromatography (eluent, dichloromethane:methanol=10:1→5:1) to give the titled compound (856 mg) as a colorless powder.

Workup

  1. extractionextracted with dichloromethane
  2. customdried
  3. distillationThe solvent was distilled off
  4. customthe residue was purified by column chromatography (eluent, dichloromethane:methanol=10:1→5:1)

Sources & evidence

ORD record
ord-77aa5a259f01496282192eb02cf93efc
Source dataset
uspto-grants-2003_06
Patent number
US06573289B1

Reaction notes

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