Acetic Acid → HCID 86724261, compound

HRID 594865Notes

Reaction equation

HRID 594865 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([OH:11])=[C:6]([C:8](=[O:10])[CH3:9])[CH:7]=1.[CH:12](=O)[CH2:13][CH3:14].N1CCCC1.C(O)(=O)C>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:7]=[C:6]2[C:5](=[CH:4][CH:3]=1)[O:11][CH:12]([CH2:13][CH3:14])[CH2:9][C:8]2=[O:10]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 527PropanalHCID 31268PyrrolidineHCID 959915'-Bromo-2'-hydroxyacetophenone

Product 1

HCID 86724261HCID 86724261, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
60 °C

Procedure

The mixture of 1-(5-bromo-2-hydroxyphenyl)ethanone (10 g, 46.50 mmol), propionaldehyde (6.7 mL, 93 mmol), pyrrolidine (3.9 mL, 47 mmol), and acetic acid (3.2 mL, 56 mmol) in toluene (20 mL) was heated to 60° C. for 18 hours. After cooling to room temperature, the mixture was concentrated in vacuo. The mixture was diluted with diethyl ether and 1M aqueous HCl. The phases were separated. The organic phase was washed with 1M aqueous NaOH, then brine. The organic phase was dried over Na2SO4, filtered, and concentrated in vacuo. Purification with silicagel column chromatography (EtOAc-hexane, a linear gradient of EtOAc from 1 to 10%) afforded 6-bromo-2-ethyl-2,3-dihydro-4H-chromen-4-one (3.92 g).

Workup

  1. temperatureAfter cooling to room temperature
  2. concentrationthe mixture was concentrated in vacuo
  3. additionThe mixture was diluted with diethyl ether and 1M aqueous HCl
  4. customThe phases were separated
  5. washThe organic phase was washed with 1M aqueous NaOH
  6. dry with materialThe organic phase was dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customPurification with silicagel column chromatography (EtOAc-hexane

Sources & evidence

ORD record
ord-57c30b101fd841b7a29ed352f546be49
Source dataset
uspto-grants-2016_01
Patent number
US09242973B2

Reaction notes

Loading…