Potassium Hydroxide → 2-(4-Methoxy-benzyloxy)-4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-benzaldehyde

HRID 479192Notes

Reaction equation

[OH:1][C:2]1[CH:9]=[C:8]([O:10][CH2:11][CH2:12][C:13]2[N:14]=[C:15]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[O:16][C:17]=2[CH3:18])[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[CH3:25][O:26][C:27]1[CH:34]=[CH:33][C:30]([CH2:31]Cl)=[CH:29][CH:28]=1.[OH-].[K+]>C([N+](CCCC)(CCCC)CCCC)CCC.S([O-])(O)(=O)=O.C1(C)C=CC=CC=1.O>[CH3:25][O:26][C:27]1[CH:34]=[CH:33][C:30]([CH2:31][O:1][C:2]2[CH:9]=[C:8]([O:10][CH2:11][CH2:12][C:13]3[N:14]=[C:15]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)[O:16][C:17]=3[CH3:18])[CH:7]=[CH:6][C:3]=2[CH:4]=[O:5])=[CH:29][CH:28]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 2-hydroxy-4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-benzaldehyde (54 mg, 0.167 mmol), 4-methoxy-benzylchloride (58 mg, 0.368 mmol), KOH (56 mg, 1 mmol) and tetrabutylammonium-hydrogensulfate (50 mg) in 6 ml toluene and 5 ml water was heated at 80° C. during 6 hours. The reaction mixture was then cooled to 0° C., washed with water/ice and brine, the aqueous layer extracted with AcOEt, the combined organic layers dried over Na2SO4 and evaporated. The crude product was purified by chromatography (SiO2; AcOEt/heptane) and the product was crystallized from heptane to yield 25 mg (34%) as a white solid.

Workup

temperatureThe reaction mixture was then cooled to 0° C.
washwashed with water/ice and brine
extractionthe aqueous layer extracted with AcOEt
dry with materialthe combined organic layers dried over Na2SO4
customevaporated
customThe crude product was purified by chromatography (SiO2; AcOEt/heptane)
customthe product was crystallized from heptane
customto yield 25 mg (34%) as a white solid

Sources & evidence

ORD record: ord-97cf77ec406246ddb71e2882abc60c15
Source dataset: uspto-grants-2003_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06642389B2

Reaction notes

Loading…