HCID 10294261, compound → HCID 10135589, compound

HRID 842120Notes

Reaction equation

HRID 842120 reaction equation
[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([CH:24]=[CH:25][C:26]=2[O:27][CH3:28])[CH2:10][C:11]2[O:12][C:13]3[C:19]([CH2:20][CH:21]=[CH2:22])=[CH:18][C:17]([Cl:23])=[CH:16][C:14]=3[N:15]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[H][H]>C(OCC)(=O)C.[Pd]>[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([CH:24]=[CH:25][C:26]=2[O:27][CH3:28])[CH2:10][C:11]2[O:12][C:13]3[C:19]([CH2:20][CH2:21][CH3:22])=[CH:18][C:17]([Cl:23])=[CH:16][C:14]=3[N:15]=2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

5

Reactant 2

HCID 10294261HCID 10294261, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 10135589HCID 10135589, compoundYield 46%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2-(3-cyclopentyloxy-4-methoxybenzyl)-5-chloro-7-allylbenzoxazole (1.2 g, 3.0 mmol) in ethyl acetate (50 ml) was hydrogenated over 0.104 g of 10% Pd on carbon catalyst in a Parr apparatus at 23 psi until hydrogen uptake ceased. The catalyst was filtered and the solvent was evaporated. The residue was recrystallized from hexane to give the title compound (0.55 g, 46%), mp 54-55° C.

Workup

  1. filtrationThe catalyst was filtered
  2. customthe solvent was evaporated
  3. customThe residue was recrystallized from hexane

Sources & evidence

ORD record
ord-3c75ed7560f14d25af5c8a66b61fd479
Source dataset
uspto-grants-2002_04
Patent number
US06372770B1

Reaction notes

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