Sodium hydride → HCID 19744904, compound

HRID 1030730Notes

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 355 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-c1b08d77ea9245ecaa8ebfd009331a9b
Source dataset: uspto-grants-1992_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05106871

Reaction notes

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