Allyl bromide → HCID 19049230, compound

HRID 1780019Notes

Reaction equation

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

Participants

Conditions

Temperature: 40 °C

Procedure

12 g of diosmetin in 100 ml of dimethylformamide and 15 ml of HMPA are added very slowly to a suspension of 4.8 g of sodium hydride in 30 ml of dimethylformamide. The mixture is then stirred at 40° C. until the evolution of gas has ceased. 17.25 g of allyl bromide are then added dropwise and the whole is heated at 60° C. for 16 hours, after which the solvents are removed by distillation under reduced pressure. The residue is taken up in dichloromethane and then chromatographed on silica using a 98% dichloromethane/2% methanol mixture as eluant. In that manner a fraction of 7.6 g of compound very fluorescent under 366 nm is recovered. An analytical sample of the title compound is prepared by recrystallisation from isopropanol, m.p.: 107° C.

Workup

temperaturethe whole is heated at 60° C. for 16 hours
customafter which the solvents are removed by distillation under reduced pressure
customchromatographed on silica using a 98% dichloromethane/2% methanol mixture as eluant
customIn that manner a fraction of 7.6 g of compound very fluorescent under 366 nm is recovered

Sources & evidence

ORD record: ord-9f84ce1eef954a8aaf15614f1b5e7ae8
Source dataset: uspto-grants-1997_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05629339

Reaction notes

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