Methyl Ethyl Ketone → 4-[4-[2-(1,3-Dioxolan-2-yl)ethyl]phenoxyacetyl]-5-methyl-2-phenyloxazole

HRID 1740918

Reaction equation

HRID 1740918 reaction equation
Br[CH2:2][C:3]([C:5]1[N:6]=[C:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[O:8][C:9]=1[CH3:10])=[O:4].[O:17]1[CH2:21][CH2:20][O:19][CH:18]1[CH2:22][CH2:23][C:24]1[CH:29]=[CH:28][C:27]([OH:30])=[CH:26][CH:25]=1.C(=O)([O-])[O-].[K+].[K+].CC(=O)CC>O>[O:17]1[CH2:21][CH2:20][O:19][CH:18]1[CH2:22][CH2:23][C:24]1[CH:29]=[CH:28][C:27]([O:30][CH2:2][C:3]([C:5]2[N:6]=[C:7]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[O:8][C:9]=2[CH3:10])=[O:4])=[CH:26][CH:25]=1

Participants

6

Reactant 4

HCID 6569Methyl Ethyl KetoneHCID 11430Potassium CarbonateHCID 149136502-Bromo-1-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethan-1-oneHCID 185461394-[2-(1,3-Dioxolan-2-yl)ethyl]phenol

Product 1

HCID 185461704-[4-[2-(1,3-Dioxolan-2-yl)ethyl]phenoxyacetyl]-5-methyl-2-phenyloxazoleYield 57%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 4-bromoacetyl-5-methyl-2-phenyloxazole (2.60 g), 4-[2-(1,3-dioxolan-2-yl)ethyl]phenol (1.82 g), potassium carbonate (1.28 g) and 2-butanone (60 ml) was stirred for 20 hours at temperatures ranging from 70 to 80° C. The reaction mixture was poured into water. Resulting crystalline precipitate was collected by filtration, which was purified by means of a silica gel column chromatography. From the fractions eluted with chloroform-methanol (100:1, v/v), 4-[4-[2-(1,3-dioxolan-2-yl)ethyl]phenoxyacetyl]-5-methyl-2-phenyloxazole (2.08 g, 57%) was obtained. Recrystallization from dichloromethane-isopropyl ether gave colorless prisms, m.p.119-120° C.

Workup

  1. customranging from 70 to 80° C
  2. filtrationResulting crystalline precipitate was collected by filtration, which
  3. customwas purified by means of a silica gel column chromatography
  4. washFrom the fractions eluted with chloroform-methanol (100:1

Sources & evidence

ORD record
ord-523da2e3e2484e7ba3cf64f59feccfb6
Source dataset
uspto-grants-1999_10
Patent number
US05972970

Linked notes

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