Sodium hydride → HCID 19744869, compound

HRID 2254244Notes

Reaction equation

[OH:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[C:4]([O:10][CH3:11])[C:3]=1[C:12](=[O:23])[CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=1.[H-].[Na+].Br[CH2:27][C:28]([O:30][CH3:31])=[O:29]>CN(C)C=O>[CH3:9][O:8][C:6]1[CH:5]=[C:4]([O:10][CH3:11])[C:3]([C:12](=[O:23])[CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=2)=[C:2]([O:1][CH2:27][C:28]([O:30][CH3:31])=[O:29])[CH:7]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Then, 30 ml of dimethylformamide was added to 5.0 g of 1-(2-hydroxy-4,6-dimethoxyphenyl)-3-(4-methoxyphenyl)-1-propanone and 420 mg of sodium hydride, and the mixture was stirred at 0° C. for 1 hour. Then, 2.6 g of methyl α-bromoacetate was added to the mixture, and the mixture was stirred at 0° C. for 1 hour and at room temperature for 1 hour to effect a reaction. After the reaction, the reaction mixture was extracted with ethyl acetate and filtered, and the solvent was removed from the filtrate by distillation. The obtained residue was subjected to the silica gel chromatography [230-400 mesh silica gel; eluting solvent=n-hexane/ethyl acetate (2/1)] and recrystallized from a mixed solvent of diethyl ether and n-hexane to obtain 5.3 g (yield=87.1%) of 1-(4,6-dimethoxy-2-methoxycarbonylmethoxyphenyl)-3-(4-methoxyphenyl)-1-propanone in the form of a colorless plate.

Workup

stirringthe mixture was stirred at 0° C. for 1 hour and at room temperature for 1 hour
customa reaction
customAfter the reaction
extractionthe reaction mixture was extracted with ethyl acetate
filtrationfiltered
customthe solvent was removed from the filtrate by distillation
customrecrystallized from a mixed solvent of diethyl ether and n-hexane

Sources & evidence

ORD record: ord-7f1154bf4ac546a4a79cc10d2332f544
Source dataset: uspto-grants-1993_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05234951

Reaction notes

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