4,5-Dihydro-2,4,4-trimethyloxazole → 4,5-Dihydro-2-[2-(2-methoxy-5-nitrophenyl)ethenyl]-4,4-dimethyloxazole

HRID 621464

Reaction equation

HRID 621464 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:4]=1[CH:5]=O.[CH3:14][C:15]1[O:16][CH2:17][C:18]([CH3:21])([CH3:20])[N:19]=1>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:4]=1[CH:5]=[CH:14][C:15]1[O:16][CH2:17][C:18]([CH3:21])([CH3:20])[N:19]=1

Participants

4

Reactant 2

HCID 744964,5-Dihydro-2,4,4-trimethyloxazoleHCID 90685Benzaldehyde, 2-methoxy-5-nitro-

Product 1

HCID 538942974,5-Dihydro-2-[2-(2-methoxy-5-nitrophenyl)ethenyl]-4,4-dimethyloxazole

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 2-methoxy-5-nitrobenzaldehyde, 16 g, (U.S. Pat. No. 4,367,234), 2,4,4-trimethyl-2-oxazoline, 30 ml, (Aldrich Chemical Company), para toluenesulfornic acid, 0.5 g, in toluene, 100 ml, is refluxed overnight under a water separator. The mixture is evaporated, the residue dissolved in diethylether, 800 ml, and washed with water. The diethyl ether layer is separated, concentrated, and filtered to give 11.1 g of 4,5-dihydro-2-[2-(2-methoxy-5-nitrophenyl)ethenyl]-4,4-dimethyloxazole after recrystallization from diisopropyl ether; mp 115°-116° C.

Workup

  1. customThe mixture is evaporated
  2. dissolutionthe residue dissolved in diethylether
  3. wash800 ml, and washed with water
  4. customThe diethyl ether layer is separated
  5. concentrationconcentrated
  6. filtrationfiltered

Sources & evidence

ORD record
ord-9a7318bef9cd4d248816b73663bb48a1
Source dataset
uspto-grants-1989_04
Patent number
US04824843

Linked notes

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