1-Methylpyrrolidine → HCID 18991985, compound

HRID 375736Notes

Reaction equation

HRID 375736 reaction equation
[CH2:1]([C:4]1[C:15]([OH:16])=[C:14]([CH3:17])[C:7]([C:8]([O:10]CC=C)=[O:9])=[C:6]([CH3:18])[C:5]=1[OH:19])[CH:2]=[CH2:3].P(OCC)(OCC)OCC.CN1CCCC1>C(OCC)(=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[OH:16][C:15]1[C:14]([CH3:17])=[C:7]([C:6]([CH3:18])=[C:5]([OH:19])[C:4]=1[CH2:1][CH2:2][CH3:3])[C:8]([OH:10])=[O:9]

Participants

6

Reactant 3

HCID 84541-MethylpyrrolidineHCID 31215Triethyl phosphiteHCID 18992147HCID 18992147, compound

Product 1

HCID 18991985HCID 18991985, compoundYield 78.6%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 5.00 g of allyl 4-allyl-3,5-dihydroxy-2,6-dimethylbenzoate in 80 ml of ethyl acetate was cooled to 0° C., and then treated with 90 mg of palladium acetate and 332 mg of triethyl phosphite. After stirring for 5 minutes, 2.04 g of N-methylpyrrolidine were added, a precipitate being formed immediately. Stirring was continued at 0° C., and then, the mixture was partitioned between ethyl acetate and 1N hydrochloric acid. The organic layer was washed with brine, dried over sodium sulfate, and the solvent was evaporated in vacuo. The residual oil was dissolved in 50 ml of ethyl acetate, and the solution was hydrogenated at atmospheric pressure for 1 hour in the presence of 100 mg of 5% palladium on charcoal. The catalyst was filtered off, and the solvent was evaporated in vacuo to yield 3.36 g of 3,5-dihydroxy-2,6-dimethyl-4-propylbenzoic acid as a coulourless oil.

Workup

  1. customa precipitate being formed immediately
  2. stirringStirring
  3. customwas continued at 0° C.
  4. customthe mixture was partitioned between ethyl acetate and 1N hydrochloric acid
  5. washThe organic layer was washed with brine
  6. dry with materialdried over sodium sulfate
  7. customthe solvent was evaporated in vacuo
  8. dissolutionThe residual oil was dissolved in 50 ml of ethyl acetate
  9. waitthe solution was hydrogenated at atmospheric pressure for 1 hour in the presence of 100 mg of 5% palladium on charcoal
  10. filtrationThe catalyst was filtered off
  11. customthe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-4a01ffd3e8564d55afc7b76adadf3105
Source dataset
uspto-grants-1996_01
Patent number
US05486466

Reaction notes

Loading…