Hydrochloric Acid → HCID 18348649, compound

HRID 2268502Notes

Reaction equation

HRID 2268502 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:13][CH2:14][C:15]([OH:17])=O)[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10].[Li+].CC([N-][CH:23]([CH3:25])[CH3:24])C.Cl>C1COCC1>[CH3:12][O:11][C:7]1[CH:6]=[C:5]2[C:4](=[C:3]([O:2][CH3:1])[C:8]=1[O:9][CH3:10])[C:15](=[O:17])[CH:14]([CH2:24][CH2:23][CH2:25][CH2:25][CH2:23][CH2:24][CH:14]1[CH2:13][C:5]3[C:4](=[C:3]([O:2][CH3:1])[C:8]([O:9][CH3:10])=[C:7]([O:11][CH3:12])[CH:6]=3)[C:15]1=[O:17])[CH2:13]2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 648603,4,5-Trimethoxyhydrocinnamic acidHCID 2724682Lithium diisopropylamide

Product 1

HCID 18348649HCID 18348649, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 3-(3,4,5-trimethoxyphenyl)propionic acid (12 g) in THF (200 ml) was dropwise added LDA (1.9 M/THF solution; 60 ml) while temperature of the reaction mixture was kept under −10° C. After being stirred at 0° C. for 3 hr, the reaction mixture was acidified to pH3 with 2N hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with water, dried and concentrated in vacuo. Polyphosphoric acid (100 ml) was added to the residue and the reaction mixture was stirred at 60° C. for 4 hr. After being cooled, the reaction mixture was diluted with water and extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium bicarbonate and then water, dried and concentrated in vacuo. The residue was purified by alumina column chromatography (ethyl acetate) and then with crystallization from ethyl acetate-hexane to yield the entitled compound (4.5 g). The compound recrystallized from ethanol gave following melting point.

Workup

  1. customwas kept under −10° C
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water
  4. customdried
  5. concentrationconcentrated in vacuo
  6. additionPolyphosphoric acid (100 ml) was added to the residue
  7. stirringthe reaction mixture was stirred at 60° C. for 4 hr
  8. temperatureAfter being cooled
  9. additionthe reaction mixture was diluted with water
  10. extractionextracted with ethyl acetate
  11. washThe organic layer was washed with saturated aqueous sodium bicarbonate
  12. dry with materialwater, dried
  13. concentrationconcentrated in vacuo
  14. customThe residue was purified by alumina column chromatography (ethyl acetate)
  15. customwith crystallization from ethyl acetate-hexane

Sources & evidence

ORD record
ord-18d14495d4dd44adbee5eb4bf5e587f2
Source dataset
uspto-grants-2001_12
Patent number
US06326369B1

Reaction notes

Loading…