Sodium hydride → HCID 19744904, compound

HRID 2254247Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[C:6]([C:11](=[O:22])[CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)=[C:5]([OH:23])[C:4]=1[CH2:24][CH:25]=[C:26]([CH3:28])[CH3:27].[H-].[Na+].Br[CH2:32][C:33]([O:35][CH3:36])=[O:34]>CN(C)C=O>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[C:6]([C:11](=[O:22])[CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)=[C:5]([O:23][CH2:32][C:33]([O:35][CH3:36])=[O:34])[C:4]=1[CH2:24][CH:25]=[C:26]([CH3:28])[CH3:27]

Participants

Conditions

Temperature: 0 °C

Procedure

Then, 30 ml of dimethylformamide was added to 5.2 g of 1-[4,6-dimethoxy-2-hydroxy-3-(3-methyl-2-butenyl)phenyl]-3-(4-methoxyphenyl)-1-propanone and 335 mg of sodium hydride, and the mixture was stirred at 0° C. for 1 hour. Then, 2.2 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 2 hours to effect 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 column chrometography [230-400 mesh silica gel; eluting solvent=n-hexane/ethyl acetate (4/1)]. to obtain 5.6 g (yield=91.0%) of 1-[4,6-dimethoxy-2-methoxycarbonylmethoxy-3-(3-methyl-2-butenyl)phenyl]-3-(4-methoxyphenyl)-1-propanone in the form of a colorless oil.

Workup

stirringthe mixture was stirred at 0° C. for 1 hour and at room temperature for 2 hours
customreaction
customAfter the reaction
extractionthe reaction mixture was extracted with ethyl acetate
filtrationfiltered
customthe solvent was removed from the filtrate by distillation

Sources & evidence

ORD record: ord-bf676d0efb2a419aba3202faa5f4f084
Source dataset: uspto-grants-1993_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05234951

Reaction notes

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