Imidazole → 2-[Dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-benzaldehyde

HRID 1064958Notes

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].N1C=CN=C1.[C:30]([Si:36]([CH3:39])([CH3:38])Cl)([CH:33]([CH3:35])[CH3:34])([CH3:32])[CH3:31]>CN(C)C=O.CCOC(C)=O>[CH3:38][Si:36]([CH3:39])([C:30]([CH3:32])([CH3:31])[CH:33]([CH3:35])[CH3:34])[O: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]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 2-hydroxy-4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-benzaldehyde (540 mg, 1.67 mmol) in 8 ml N,N-dimethylformamide cooled to 0° C., were added 398 mg (5.85 mol) imidazole and 1.1 ml (5.85 mmol) thexyl-dimethylchlorosilane. The reaction mixture was stirred 50 minutes at 0° C., diluted with AcOEt, washed with water/ice, HCl (1M)/ice and brine and the aqueous layer was extracted with AcOEt. The combined organic layers were dried over Na2SO4 and evaporated. Chromatography (SiO2; AcOEt/heptane) delivered 346 mg (45%) of the title compound as an oil.

Workup

washwashed with water/ice, HCl (1M)/ice and brine
extractionthe aqueous layer was extracted with AcOEt
dry with materialThe combined organic layers were dried over Na2SO4
customevaporated

Sources & evidence

ORD record: ord-c97caa36897e46ad9ce2e0d88986d714
Source dataset: uspto-grants-2005_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06969725B2

Reaction notes

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