Hydrochloric Acid → HCID 19358464, compound

HRID 377324Notes

Reaction equation

HRID 377324 reaction equation
[C:1]1([C:7]2[N:8]=[C:9]([C:18]3[CH:39]=[CH:38][CH:37]=[CH:36][C:19]=3[CH:20](O)[C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([O:27]CC4C=CC=CC=4)[CH:22]=3)[O:10][C:11]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.O.[H][H]>C(OCC)(=O)C.CO.[Pd]>[C:1]1([C:7]2[N:8]=[C:9]([C:18]3[CH:39]=[CH:38][CH:37]=[CH:36][C:19]=3[CH2:20][C:21]3[CH:22]=[C:23]([OH:27])[CH:24]=[CH:25][CH:26]=3)[O:10][C:11]=2[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 19358493HCID 19358493, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 19358464HCID 19358464, compoundYield 29.1%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2-(4,5-diphenyl-2-oxazolyl)-3'-benzyloxybenzhydrol (650 mg) in ethyl acetate (3 ml), methanol (3 ml), and 10% hydrogen chloride in methanol (0.3 ml) was stirred in the presence of 10% palladium on carbon--water (50/50 wt. % ) (400 mg) and hydrogen at atmospheric pressure at room temperature for 10 hours. The reaction mixture was filtered and the filtrate was evaporated in vacuo. The residue was chromatographed (toluene--ethyl acetate) over silica gel to afford 3-[[2-(4,5-diphenyl-2-oxazolyl)phenyl]methyl]phenol (150 mg) as a colorless powder.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customthe filtrate was evaporated in vacuo
  3. customThe residue was chromatographed (toluene--ethyl acetate) over silica gel

Sources & evidence

ORD record
ord-a37fd65351984db68c4873d66881b18d
Source dataset
uspto-grants-2000_02
Patent number
US06025375

Reaction notes

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