HCID 135545348, compound → HCID 135442595, compound

HRID 858254Notes

Reaction equation

HRID 858254 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]3[C:16]([C:17]([CH3:19])=[CH2:18])=[CH:15][C:14]([OH:20])=[CH:13][C:11]=3[N:12]=2)=[CH:4][CH:3]=1>CCOC(C)=O.C(O)C.[Pd]>[OH:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[O:9][C:10]3[C:16]([CH:17]([CH3:18])[CH3:19])=[CH:15][C:14]([OH:20])=[CH:13][C:11]=3[N:12]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 1

HCID 135545348HCID 135545348, compound

Product 1

HCID 135442595HCID 135442595, compoundYield 90%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-(4-Hydroxyphenyl)-7-isopropenyl-1,3-benzoxazol-5-ol (64 mg, 0.24 mmol) was dissolved in a mixture of EtOAc (5 mL) and absolute ethanol (5 mL) and placed under an inert atmosphere with argon. To this mixture was added 10% Pd—C (25 mg). The solution was hydrogenated on a Parr apparatus at 25 psi for 3 h. The solution was filtered through celite and rinsed with ethanol. The filtrate was concentrated and the residue purified by flash chromatography (50% EtOAc/petroleum ether) to give (58 mg, 90% yield) of the product as a tan solid, m.p. 200° C.; MS m/e 270 (M+H)+.

Workup

  1. filtrationThe solution was filtered through celite
  2. washrinsed with ethanol
  3. concentrationThe filtrate was concentrated
  4. customthe residue purified by flash chromatography (50% EtOAc/petroleum ether)

Sources & evidence

ORD record
ord-0f03caac04ff4ed2b3fa26e5aef19474
Source dataset
uspto-grants-2006_12
Patent number
US07148247B2

Reaction notes

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