Allyl bromide → HCID 58774160, compound

HRID 714488Notes

Reaction equation

HRID 714488 reaction equation
[CH:1]1[C:6]([C@H:7]2[O:16][C:15]3[CH:14]=[C:13]([OH:17])[CH:12]=[C:11]([OH:18])[C:10]=3[CH2:9][C@H:8]2[OH:19])=[CH:5][C:4]([OH:20])=[C:3]([OH:21])[CH:2]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:28](Br)[CH:29]=[CH2:30]>CC(C)=O>[CH2:30]([O:21][C:3]1[CH:2]=[CH:1][C:6]([CH:7]2[CH:8]([OH:19])[CH2:9][C:10]3[C:11]([OH:18])=[CH:12][C:13]([OH:17])=[CH:14][C:15]=3[O:16]2)=[CH:5][C:4]=1[OH:20])[CH:29]=[CH2:28].[CH2:30]([O:20][C:4]1[CH:5]=[C:6]([CH:7]2[CH:8]([OH:19])[CH2:9][C:10]3[C:11]([OH:18])=[CH:12][C:13]([OH:17])=[CH:14][C:15]=3[O:16]2)[CH:1]=[CH:2][C:3]=1[OH:21])[CH:29]=[CH2:28]

Participants

6

Reactant 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 72276(-)-Epicatechin

Product 2

HCID 58774160HCID 58774160, compoundHCID 89405955HCID 89405955, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a mixture of (−)-epicatechin (1.16 g, 4 0 mmol) and potassium carbonate (1.10 g, 8.0 mmol) in dry acetone was added allyl bromide (0.41 mL, 4.8 mmol). The reaction was heated at reflux, under nitrogen, protected from light with vigorous stirring for 4 h. The reaction was filtered and concentrated onto silica gel. The crude product was purified on a Biotage 50 g silica gel column eluting with a gradient of 40-70% ethyl acetate/hexane and then 70% ethyl acetate/hexane. The major peak, corresponding to a mixture of monoallylated products, was isolated. This mixture was further purified by preparative reverse phase HPLC using a gradient of 1:9 to 8:2 acetonitrile/(0.2% formic acid/water) over 20 min. The appropriate fractions were frozen and lyophilized to give as white powders to provide 2-(4-Allyloxy-3-hydroxy-phenyl)-chroman-3,5,7-triol and 2-(3-Allyloxy-4-hydroxy-phenyl)-chroman-3,5,7-triol.

Workup

  1. temperatureThe reaction was heated
  2. temperatureat reflux, under nitrogen
  3. filtrationThe reaction was filtered
  4. concentrationconcentrated onto silica gel
  5. customThe crude product was purified on a Biotage 50 g silica gel column
  6. washeluting with a gradient of 40-70% ethyl acetate/hexane
  7. additionThe major peak, corresponding to a mixture of monoallylated products
  8. customwas isolated
  9. customThis mixture was further purified by preparative reverse phase HPLC
  10. customover 20 min
  11. temperatureThe appropriate fractions were frozen
  12. customto give as white powders

Sources & evidence

ORD record
ord-312273ce9191426c8477625c8a84b0d4
Source dataset
uspto-grants-2015_11
Patent number
US09187448B2

Reaction notes

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