Epichlorohydrin → HCID 86618198, compound

HRID 1694659Notes

Reaction equation

HRID 1694659 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:20])[C:7]([C:12]3[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=3)=[CH:8][O:9]2)=[CH:4][CH:3]=1.[CH2:21]([CH:23]1[O:25][CH2:24]1)Cl.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH3:19][O:18][C:15]1[CH:16]=[CH:17][C:12]([C:7]2[C:6](=[O:20])[C:5]3[C:10](=[CH:11][C:2]([O:1][CH2:21][CH:23]4[CH2:24][O:25]4)=[CH:3][CH:4]=3)[O:9][CH:8]=2)=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 7835EpichlorohydrinHCID 11430Potassium CarbonateHCID 5280378Formononetin

Product 1

HCID 86618198HCID 86618198, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 7-hydroxy-3-(4-methoxyphenyl)chromen-4-one (0.86 g, 3.21 mmol), epichlorohydrin (1.25 ml, 16 mmol) and potassium carbonate (0.89 g, 6.42 mmol) in dimethylformamide (20 ml) was stirred at 80° C. for 3 hours. After removing solvent under reduced pressure, water was added to the residue, and the precipitate filtered off and washed with water. The crude product was purified by chromatography on silica gel, eluting with ethyl acetate/hexanes. (1:4 to 2:3), to afford 3-(4-methoxyphenyl)-7-(oxiran-2-ylmethoxy)chromen-4-one.

Workup

  1. customAfter removing solvent under reduced pressure, water
  2. additionwas added to the residue
  3. filtrationthe precipitate filtered off
  4. washwashed with water
  5. customThe crude product was purified by chromatography on silica gel
  6. washeluting with ethyl acetate/hexanes

Sources & evidence

ORD record
ord-80d9362efedb46a28c766cdb0adabcba
Source dataset
uspto-grants-2012_04
Patent number
US08158810B2

Reaction notes

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