5-Chloro-2-(2-chlorophenyl)-7-(3-hydroxy-1-butynyl)-benzoxazole → 5-Chloro-2-(2-chlorophenyl)-7-(3-hydroxybutyl)-benzoxazole

HRID 842101Notes

Reaction equation

HRID 842101 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:18]#[C:19][CH:20]([OH:22])[CH3:21])[C:5]2[O:9][C:8]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[Cl:16])=[N:7][C:6]=2[CH:17]=1>C(OCC)(=O)C.[Ni]>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:18][CH2:19][CH:20]([OH:22])[CH3:21])[C:5]2[O:9][C:8]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[Cl:16])=[N:7][C:6]=2[CH:17]=1

Participants

4

Reactant 1

HCID 46392555-Chloro-2-(2-chlorophenyl)-7-(3-hydroxy-1-butynyl)-benzoxazole

Product 1

HCID 51467885-Chloro-2-(2-chlorophenyl)-7-(3-hydroxybutyl)-benzoxazoleYield 74.2%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8857Ethyl AcetateSolvent

Procedure

11.10 g (33.4 mmol) of 5-chloro-2-(2-chlorophenyl)-7-(3-hydroxy-1-butynyl)-benzoxazole was hydrogenated in 220 ml of ethyl acetate with 3.7 g of neutral Raney-nickel as catalyst. After 2.5 hours, H2 uptake had ceased and the nickel was filtered off. The solvent was removed in vacuo and the residue crystallized from di-isopropyl ether at 0° C. to give 8.33 g (74.2%) of title compound, mp 85-7° C. A second crop of 0.47 g (4.2%) was recovered.

Workup

  1. filtrationthe nickel was filtered off
  2. customThe solvent was removed in vacuo
  3. customthe residue crystallized from di-isopropyl ether at 0° C.

Sources & evidence

ORD record
ord-18df289ccff44d58a1a2ba76b323d8b1
Source dataset
uspto-grants-2002_04
Patent number
US06372770B1

Reaction notes

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