Toluene → HCID 11727814, compound

HRID 233330Notes

Reaction equation

HRID 233330 reaction equation
Br[CH:2]([CH2:6][C:7]1[CH:8]=[CH:9][C:10]([O:13][CH2:14][C:15]2[N:16]=[C:17]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[O:18][C:19]=2[CH3:20])=[N:11][CH:12]=1)[C:3]([O-:5])=[O:4].[CH2:27]1CCN2C(=NCCC2)CC1.C1(C)C=CC=CC=1>O>[CH3:20][C:19]1[O:18][C:17]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[N:16][C:15]=1[CH2:14][O:13][C:10]1[CH:9]=[CH:8][C:7](/[CH:6]=[CH:2]/[C:3]([O:5][CH3:27])=[O:4])=[CH:12][N:11]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 23361372HCID 23361372, compound

Product 1

HCID 11727814HCID 11727814, compoundYield 83.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2-bromo-3-[2-(5-methyl-2-phenyl-4-oxazolyl-methoxy)-5-pyridyl]propionate (4.00 g), 1,8-diazabicyclo[5,4,0]-7-undecene (1.41 g) and toluene (80 ml) was stirred 2 hours at 90°-100° C. The reaction mixture was poured into water and extracted with ethyl acetate. The ethyl acetate layer was washed with water and dried (MgSO4), then the solvent was distilled off under reduced pressure. The residual oily product was subjected to a silica gel chromatography. From the fractions eluted with ethyl acetate-hexane (1:3, v/v) was obtained methyl (E)-3-[2-(5-methyl-2-phenyl-4-oxazolylmethoxy)-5-pyridyl]acrylate (2.71 g, 83%). Recrystallization from diethyl ether-isopropyl ether gave colorless prisms, m.p. 116°-117° C.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with water
  3. dry with materialdried (MgSO4)
  4. distillationthe solvent was distilled off under reduced pressure
  5. washFrom the fractions eluted with ethyl acetate-hexane (1:3

Sources & evidence

ORD record
ord-3163d0f918484bcf9e8a7e789fbfaf56
Source dataset
uspto-grants-1997_01
Patent number
US05591862

Reaction notes

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