Methanol → AC-Pro-ome

HRID 579832Notes

Reaction equation

HRID 579832 reaction equation
CCCCCCCCCCCCCCC.C[OH:17].[C:18]([N:21]1[CH2:25][CH2:24][CH:23]=[CH:22]1)(=[O:20])[CH3:19].[O:26]1[CH2:30]CC[CH2:27]1>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:27][O:26][C:30](=[O:17])[C@@H:22]1[CH2:23][CH2:24][CH2:25][N:21]1[C:18](=[O:20])[CH3:19]

Participants

6

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 12391PentadecaneHCID 10909522N-Acetyl-2-pyrroline3×

Product 1

HCID 11019314AC-Pro-omeYield 18.5%

Reagents, catalysts & solvents 1

HCID 178418476HCID 178418476, compoundCatalyst

Conditions

Temperature
100 °C

Procedure

A 70 mL stainless steel high pressure reactor having a Pyrex glass liner nd a magnetic stir bar was charged with 5 mL of tetrahydrofuran, 0.5 mmol of n-pentadecane internal standard, 0.5 mmol of CH3OH, 45.8 mg of (PPh3)2PdCl2, and 53.3 mg of N-acetyl-2-pyrroline. The reactor was pressurized with 700 psi of CO and 300 psi of H2 at room temperature, and the reaction mixture was stirred at 100° C. for 18 hours. Thereafter, the reactor was cooled to room temperature and vented to atmospheric pressure. The product mixture was analyzed by gas chromatography, and the analysis indicated 99.0% conversion of N-acetyl-2-pyrroline. The reactor was pressurized with 700 psi of CO and 300 psi of H2 at room temperature, and the reaction mixture was stirred at 100° C. for 18 hours. Thereafter, the reactor was cooled to room temperature and vented to atmospheric pressure. The product mixture was analyzed by gas chromatography, and the analysis indicated 99.0% conversion of N-acetyl-2-pyrroline and 18.5% yield of N-acetylproline methyl ester.

Workup

  1. customA 70 mL stainless steel high pressure reactor having
  2. customwas pressurized with 700 psi of CO and 300 psi of H2 at room temperature
  3. temperatureThereafter, the reactor was cooled to room temperature
  4. customwas pressurized with 700 psi of CO and 300 psi of H2 at room temperature
  5. stirringthe reaction mixture was stirred at 100° C. for 18 hours
  6. temperatureThereafter, the reactor was cooled to room temperature

Sources & evidence

ORD record
ord-981a84625ac140cb98006d122f0e4f35
Source dataset
uspto-grants-1988_06
Patent number
US04749786

Reaction notes

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