Potassium Hydroxide → 3-Methyl-4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-benzaldehyde

HRID 479186Notes

Reaction equation

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

Participants

Conditions

Temperature: 0 °C

Procedure

4-Hydroxy-3-methylbenzaldehyde (9 g, 66.10 mmol), methanesulfonic acid 2-(5-methyl-2-phenyl-oxazol-4-yl)-ethyl ester [PCT Int. Appl. (2000) WO0008002] (22.5 g, 80 mmol), KOH (80 mmol, 4.48 g) and tetrabutylammonium-hydrogensulfate (2 g) in 400 ml toluene/100 ml water were heated at 80° C. during 17 hours. The reaction mixture was then cooled to 0° C., washed with water/ice and brine, the aqueous layer extracted with tBuOMe, 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 CH2Cl2/heptane to yield 15 g (72%) of the title compound as a white solid.

Workup

washwashed with water/ice and brine
extractionthe aqueous layer extracted with tBuOMe
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 CH2Cl2/heptane

Sources & evidence

ORD record: ord-9435fb575c37436b8694411a1551cb17
Source dataset: uspto-grants-2003_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06642389B2

Reaction notes

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