Acetic Acid → 8-Allyl-7-methoxy-2-methoxymethyl-2-methyl-4-oxochromane

HRID 494955Notes

Reaction equation

HRID 494955 reaction equation
[CH2:1]([C:4]1[C:5]([OH:15])=[C:6]([C:12](=[O:14])[CH3:13])[CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[CH:2]=[CH2:3].[CH3:16][O:17][CH2:18][C:19](=O)[CH3:20].N1CCCC1.C(O)(=O)C>C1(C)C=CC=CC=1>[CH2:1]([C:4]1[C:9]([O:10][CH3:11])=[CH:8][CH:7]=[C:6]2[C:5]=1[O:15][C:19]([CH2:18][O:17][CH3:16])([CH3:20])[CH2:13][C:12]2=[O:14])[CH:2]=[CH2:3]

Participants

6

Reactant 4

HCID 176Acetic Acid2×HCID 22172Methoxyacetone2×HCID 31268Pyrrolidine2×HCID 140448303'-Allyl-2'-hydroxy-4'-methoxyacetophenone

Product 1

HCID 576827828-Allyl-7-methoxy-2-methoxymethyl-2-methyl-4-oxochromaneYield 32.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

445 mg of 3′-allyl-2′-hydroxy-4′-methoxyacetophenone and 0.57 g of methoxyacetone were dissolved in 10 ml of toluene. Thereafter, 0.19 g of pyrrolidine and 0.19 ml of acetic acid were added to the reaction solution. Thereafter, the reaction solution was heated to reflux using Dean-Stark for 1 hour. Thereafter, the reaction solution was cooled to a room temperature. 1.14 g of methoxyacetone, 0.38 g of pyrrolidine, and 0.38 ml of acetic acid were added to the reaction solution, and the obtained mixture was further heated to reflux overnight. The reaction solution was cooled to a room temperature and then concentrated under a reduced pressure. The residue was diluted with ethyl acetate, and then successively washed with 2 N hydrochloric acid, a 1 N sodium hydroxide aqueous solution, water, and a saturated sodium chloride aqueous solution. The organic layer was dried over magnesium sulfate and then concentrated under a reduced pressure. The residue was purified by silica gel column chromatography (hexane-ethyl acetate), so as to obtain 194 mg of the subject compound.

Workup

  1. temperatureThereafter, the reaction solution was heated
  2. temperatureto reflux
  3. customfor 1 hour
  4. temperaturethe obtained mixture was further heated
  5. temperatureto reflux overnight
  6. temperatureThe reaction solution was cooled to a room temperature
  7. concentrationconcentrated under a reduced pressure
  8. additionThe residue was diluted with ethyl acetate
  9. washsuccessively washed with 2 N hydrochloric acid
  10. dry with materialThe organic layer was dried over magnesium sulfate
  11. concentrationconcentrated under a reduced pressure
  12. customThe residue was purified by silica gel column chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-66cd42b3a4e94e53873611175aa01e64
Source dataset
uspto-grants-2009_05
Patent number
US07538123B2

Reaction notes

Loading…