Toluene → HCID 54227540, compound

HRID 1377653Notes

Reaction equation

Br[CH:2]([CH2:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH2:15][CH2:16][C:17]2[N:18]=[C:19]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[O:20][C:21]=2[CH3:22])=[CH:10][CH:9]=1)[C:3]([O:5][CH3:6])=[O:4].C1CCN2C(=NCCC2)CC1.C1(C)C=CC=CC=1>C(OCC)(=O)C>[CH3:22][C:21]1[O:20][C:19]([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)=[N:18][C:17]=1[CH2:16][CH2:15][O:14][C:11]1[CH:10]=[CH:9][C:8]([CH:7]=[CH:2][C:3]([O:5][CH3:6])=[O:4])=[CH:13][CH:12]=1

Participants

Conditions

Temperature: 70 °C

Procedure

A mixture of methyl 2-bromo-3-[4-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]phenyl]propionate (15.0 g), 1,8-diazabicyclo[5,4,0]-7-undecene (DBU) (6.2 g) and toluene (200 ml) was stirred for 2 hours at 70° C. The reaction mixture was poured into ethyl acetate (200 ml), which was washed with 2N HCl and a saturated aqueous saline solution, followed by drying (MgSO4). The solvent was distilled off under reduced pressure to leave methyl 4-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]cinnamate (10.8 g, 88%). Recrystallization from ethyl acetate--hexane colorless needles, m.p.114°-115° C.

Workup

washwas washed with 2N HCl
dry with materialby drying (MgSO4)
distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record: ord-701d3c72754a48c485b99a214f3db6ba
Source dataset: uspto-grants-1997_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05665748

Reaction notes

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