Ethyl Acetate → HCID 12044211, compound

HRID 990082Notes

Reaction equation

HRID 990082 reaction equation
[CH2:1]1[O:5][C:4]2[CH:6]=[C:7]([OH:10])[CH:8]=[CH:9][C:3]=2[O:2]1.C(=O)([O-])[O-].[K+].[K+].[CH2:17]1[O:19][C@@H:18]1[CH2:20]OS(C1C=C([N+]([O-])=O)C=CC=1)(=O)=O.C(OCC)(=O)C>CC(=O)CC>[O:19]1[CH2:17][C@H:18]1[CH2:20][O:10][C:7]1[CH:8]=[CH:9][C:3]2[O:2][CH2:1][O:5][C:4]=2[CH:6]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 68289SesamolHCID 146490Benzenesulfonic acid, 3-nitro-, (2S)-2-oxiranylmethyl ester

Product 1

HCID 12044211HCID 12044211, compoundYield 57.4%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of sesamol (2.49 g, 18.02 mmol), potassium carbonate (2.74 g, 19.83 mmol) and (2S)-(+)-glycidyl-3-nitrobenzenesulfonate (4.67 g, 18.02 mmol) in 2-butanone (50 mL) was heated to reflux for 18 h. To the cooled reaction mixture was added 35 mL of ethyl acetate and the solids were remove by vacuum filtration. The filtrate was evaporated in vacuo and the residue was taken up into ethyl acetate (65 mL). The solution was washed with aqueous sodium bicarbonate (2×), and water (2×), dried (Na2SO4), filtered and evaporated in vacuo. The residue was purified by flash chromatography (silica gel, 50% diethyl ether/hexane) to leave 2.01 g of the title compound.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 18 h
  3. customTo the cooled reaction mixture
  4. customthe solids were remove by vacuum filtration
  5. customThe filtrate was evaporated in vacuo
  6. washThe solution was washed with aqueous sodium bicarbonate (2×), and water (2×)
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. customevaporated in vacuo
  10. customThe residue was purified by flash chromatography (silica gel, 50% diethyl ether/hexane)

Sources & evidence

ORD record
ord-41c49f052d81413c86976e8645eadc8b
Source dataset
uspto-grants-2002_10
Patent number
US06458817B1

Reaction notes

Loading…