Dimethylformamide → 5-(4,4-Dimethyl-4,5-dihydrooxazol-2-yl)-2-methoxybenzaldehyde

HRID 850435Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]([C:10]2[O:11][CH2:12][C:13]([CH3:16])([CH3:15])[N:14]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].C1C[O:20][CH2:19]C1.C([Li])CCC.CN(C=O)C>O.CCCCCC>[CH3:15][C:13]1([CH3:16])[CH2:12][O:11][C:10]([C:4]2[CH:5]=[CH:6][C:7]([O:8][CH3:9])=[C:2]([CH:3]=2)[CH:19]=[O:20])=[N:14]1

Participants

Conditions

Temperature: -78 °C

Procedure

2-(3-Bromo-4-methoxyphenyl)-4,4-dimethyl-4,5-dihydrooxazole (2.1 g, 7.4 mmol) and THF (15 ml) were mixed, and this solution was cooled to -78° C. A hexane solution (1.6M, 4.75 ml) of n-butyllithium (7.6 mmol) was added, and the mixture was stirred for 2 hours. DMF (1.16 ml, 15 mmol) was added and the mixture was stirred for 20 minutes. Water (20 ml) was added to stop the reaction. The aqueous layer was extracted twice with ethyl acetate (20 ml). The organic layers were combined, and washed with saturated brine (30 ml). This solution was dried over anhydrous magnesium sulfate, and the drying agent was filtered off. The filtrate was concentrated under reduced pressure, and the obtained residue was purified by column chromatography (hexane/ethyl acetate=3/1-1/3) to give 5-(4,4-dimethyl-4,5-dihydrooxazole-2-yl)-2-methoxybenzaldehyde (0.71 g, 41%) as colorless transparent crystals.

Workup

stirringthe mixture was stirred for 20 minutes
customthe reaction
extractionThe aqueous layer was extracted twice with ethyl acetate (20 ml)
washwashed with saturated brine (30 ml)
dry with materialThis solution was dried over anhydrous magnesium sulfate
filtrationthe drying agent was filtered off
concentrationThe filtrate was concentrated under reduced pressure
customthe obtained residue was purified by column chromatography (hexane/ethyl acetate=3/1-1/3)

Sources & evidence

ORD record: ord-3e10c1049cdb44eab19e34cb31cf7c73
Source dataset: uspto-grants-2000_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06017919

Reaction notes

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