Methanol → 4-(5-Chloro-2-(2-chlorophenyl)benzoxazol-7-yl)butan-2-one

HRID 842102Notes

Reaction equation

HRID 842102 reaction equation
[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.CO.O>CC(C)=O.ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:18][CH2:19][C:20](=[O: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

6

Reactant 3

HCID 887MethanolHCID 962WaterHCID 51467885-Chloro-2-(2-chlorophenyl)-7-(3-hydroxybutyl)-benzoxazole

Product 1

HCID 51467894-(5-Chloro-2-(2-chlorophenyl)benzoxazol-7-yl)butan-2-oneYield 65.8%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6344DichloromethaneSolvent

Procedure

7.54 ml of Kiliani solution (30.2 mmol of 0) was added over 6 minutes to a solution of 8.80 g (26.2 mmol) of 5-chloro-2-(2-chlorophenyl)-7-(3-hydroxybutyl)-benzoxazole in 90 ml of acetone at −5° to 0° C. After 2.5 hours, 5 ml of methanol and 50 ml of water was added. The acetone was removed in vacuo, the solid suspended, collected, washed with 0.1 N sulfuric acid until colorless and water and dried to give 8.68 g of crude product, which was dissolved in 35 ml of dichloromethane and filtered through 260 g of silica gel. A first fraction of 100 mg was discarded then 5.94 g were recovered and crystallized from di-isopropyl ether to give 5.76 g (65.8%) of title compound, mp 109-10° C.

Workup

  1. customThe acetone was removed in vacuo
  2. customcollected
  3. washwashed with 0.1 N sulfuric acid until colorless and water
  4. customdried
  5. customto give 8.68 g of crude product, which
  6. filtrationfiltered through 260 g of silica gel
  7. custom5.94 g were recovered
  8. customcrystallized from di-isopropyl ether

Sources & evidence

ORD record
ord-2f23b41265994cf6ad1123220bf6be35
Source dataset
uspto-grants-2002_04
Patent number
US06372770B1

Reaction notes

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