5-Chloro-2-(2-chlorophenyl)-7-(3-hydroxy-1-propynyl)-benzoxazole → 5-Chloro-2-(2-chlorophenyl)-7-(3-hydroxy-propyl)-benzoxazole

HRID 842129Notes

Reaction equation

HRID 842129 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:18]#[C:19][CH2:20][OH: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.[H][H]>C(OCC)(=O)C.[Ni]>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:18][CH2:19][CH2:20][OH: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

5

Reactant 2

HCID 226182815-Chloro-2-(2-chlorophenyl)-7-(3-hydroxy-1-propynyl)-benzoxazoleHCID 178418361HCID 178418361, compound

Product 1

HCID 226182825-Chloro-2-(2-chlorophenyl)-7-(3-hydroxy-propyl)-benzoxazole

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A suspension of 11.07 g (34.8 mmol) of 5-chloro-2-(2-chlorophenyl)-7-(3-hydroxy-1-propynyl)-benzoxazole in 120 ml of ethyl acetate was treated with 3.70 g of neutral Raney-nickel. After the hydrogen uptake ceased, the nickel was filtered off and washed, and the solution evaporated in vacuo. Crystallization from dichloromethane/di-isopropyl ether gave the title compound in two crops (6.12 g (54.6%) and 1.61 g (14.4%)), mp 82-4° C.

Workup

  1. filtrationthe nickel was filtered off
  2. washwashed
  3. customthe solution evaporated in vacuo
  4. customCrystallization from dichloromethane/di-isopropyl ether

Sources & evidence

ORD record
ord-ed369de8ebb845ba8f5d71ad9fcb207a
Source dataset
uspto-grants-2002_04
Patent number
US06372770B1

Reaction notes

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