Hydrochloric Acid → HCID 9965857, compound

HRID 1375699Notes

Reaction equation

HRID 1375699 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11](=[O:17])[CH2:12][CH2:13][C:14]([OH:16])=[O:15])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].O[C:19]1[CH:20]=C(C(=O)CCC(O)=O)C=[CH:23][C:24]=1OC.C([O-])([O-])=O.[K+].[K+].BrC1CCCC1.Cl>Br.O.CN(C=O)C.CCOC(C)=O>[CH:1]1([O:2][C:3]2[CH:4]=[C:5]([C:11](=[O:17])[CH2:12][CH2:13][C:14]([OH:16])=[O:15])[CH:6]=[CH:7][C:8]=2[O:9][CH3:10])[CH2:23][CH2:24][CH2:19][CH2:20]1

Participants

10

Reactant 5

HCID 313Hydrochloric AcidHCID 8728BromocyclopentaneHCID 11430Potassium CarbonateHCID 2193904-(3,4-Dimethoxyphenyl)-4-oxobutanoic acidHCID 12467403HCID 12467403, compound

Product 1

HCID 9965857HCID 9965857, compoundYield 14.4%

Reagents, catalysts & solvents 4

HCID 260Hydrogen BromideSolventHCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

4.7 g (0.019 mol) of 4-(3,4-dimethoxyphenyl)-4-oxo-butanoic acid (FN 549) are dissolved in 50 ml of 47% HBr in water, heating to reflux for one hour until the reaction compound disappears. The reaction solution is concentrated to dryness, adding acetonitrile several times, and then the dark pitch is extracted hot several times with ethyl ether. On concentrating the organic solution to dryness, 3.3 g of crude product are obtained, which can be used as such in the next reaction. 3.3 g (0.015 mol) of crude 4-(3-hydroxy-4-methoxyphenyl)-4-oxo-butanoic acid (FN 551) are suspended in 30 ml of anhydrous DMF with 6.2 g (0.045 mol) of K2CO3, left under stirring for 30 minutes, and then added with 2.4 ml (0.0225 mol) of bromocyclopentane and heated at 70° C. for 4 hours under a nitrogen atmosphere. After one night at room temperature, the reaction mixture is dried under reduced pressure and the residue obtained is divided between HCl 2N and EtOAc, washing the organic phase with water. The reaction mixture is anhydrified on anhydrous sodium sulphate and evaporated to dryness, obtaining a dark oil which is chromatographed on a silica gel column, eluting with n-hexane/EtOAc. After crystallisation, the same mixture of solvents yields fractions containing the dried product. 0.63 g of product are obtained. Yield 14%.

Workup

  1. temperatureheating
  2. temperatureto reflux for one hour until the reaction compound
  3. concentrationThe reaction solution is concentrated to dryness
  4. additionadding acetonitrile several times
  5. extractionthe dark pitch is extracted hot several times with ethyl ether
  6. concentrationOn concentrating the organic solution to dryness, 3.3 g of crude product
  7. customare obtained
  8. customsuch in the next reaction
  9. waitleft
  10. waitAfter one night at room temperature
  11. customthe reaction mixture is dried under reduced pressure
  12. customthe residue obtained
  13. washwashing the organic phase with water
  14. customevaporated to dryness
  15. customobtaining a dark oil which
  16. customis chromatographed on a silica gel column
  17. washeluting with n-hexane/EtOAc
  18. customAfter crystallisation
  19. additionthe same mixture of solvents
  20. customyields fractions
  21. additioncontaining the dried product

Sources & evidence

ORD record
ord-350d6a34e3d04ad59ee9bf5012478f36
Source dataset
uspto-grants-2007_01
Patent number
US07169808B2

Reaction notes

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