Ethyl bromoacetate → HCID 906979, compound

HRID 1882307Notes

Reaction equation

HRID 1882307 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:18])[C:7]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[CH:8][O:9]2)=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].C[CH2:26][O:27][C:28]([CH2:30]Br)=[O:29]>CC(C)=O>[CH3:26][O:27][C:28](=[O:29])[CH2:30][O:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:18])[C:7]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[CH:8][O:9]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 53768917-Hydroxyisoflavone

Product 1

HCID 906979HCID 906979, compoundYield 72.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a mixture of 7-Hydroxy isoflavone (35 grams, 147 mmol), anhydrous K2CO3 (84 grams, 608 mmol) in anhydrous acetone (500 mL) was added ethyl bromo acetate (29 grams, 174 mmol) and refluxed for 8 hours. Acetone was distilled and water (500 mL) was added. Crude 49 was filtered, dried, and recrystallized from toluene to give pure 49 (33 grams, 72.4%) as a white shining powder. The melting point was found to be 105-106.5° C. The structure was confirmed with IR and NMR. IHNMR (CDCl3) δ 1.31 (t, 3H, OCH2, CH3), 4.30 (q, 2H, OCH2, CH3), 4.70 (s, 2H, OCH2), 6.84 (d, 1H, Ar), 7.05 (dd, 1H, Ar), 7.41 (m, 3H, Ar), 7.57 (m, 2H, Ar), 7.97 (s, 1H, Pyran), 8.24 (d, 1H, Ar).

Workup

  1. temperaturerefluxed for 8 hours
  2. distillationAcetone was distilled
  3. additionwater (500 mL) was added
  4. filtrationCrude 49 was filtered
  5. customdried
  6. customrecrystallized from toluene

Sources & evidence

ORD record
ord-4b9ae7b7f899474ea6055aea5aadc986
Source dataset
uspto-grants-2012_11
Patent number
US08318973B2

Reaction notes

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