Methanol → AC-Pro-ome

HRID 579826Notes

Reaction equation

HRID 579826 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>>[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

5

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 12391PentadecaneHCID 10909522N-Acetyl-2-pyrroline2×

Product 1

HCID 11019314AC-Pro-omeYield 7.6%

Conditions

Temperature
100 °C

Procedure

A 70 mL stainless steel high pressure reactor having a Pyrex glass liner and a magnetic stir bar was charged with 5 mL of tetrahydrofuran, 0.5 mmol of n-pentadecane internal standard, 0.5 mmol of CH3OH, 6.5 mg of Co2 (CO)8, and 54.9 mg of N-acetyl-2-pyrroline. The reactor was pressurized with 1320 psi of CO and 300 psi of H2 at room temperature, and the reaction mixture ws stirred at 100° C. for 22 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 82.3% conversion of N-acetyl-2-pyrroline and 7.6% yield of N-acetylproline methyl ester.

Workup

  1. customA 70 mL stainless steel high pressure reactor having
  2. customwas pressurized with 1320 psi of CO and 300 psi of H2 at room temperature
  3. temperatureThereafter, the reactor was cooled to room temperature

Sources & evidence

ORD record
ord-eac8fd69de604f999c7de9cbc9a29ec5
Source dataset
uspto-grants-1988_06
Patent number
US04749786

Reaction notes

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