Methanol → AC-Pro-ome

HRID 579833Notes

Reaction equation

HRID 579833 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 36.4%

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, 1.0 mmol of CH3OH, 82.6 mg of (PPh3)2PdCL2, and 107.2 mg of N-acetyl-2-pyrroline. The reactor was pressurized to 1000 psi with CO 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 98.4% conversion of N-acetyl-2-pyrroline and 36.4% yield of N-acetylproline methyl ester.

Workup

  1. customA 70 mL stainless steel high pressure reactor having
  2. customwas pressurized to 1000 psi with CO at room temperature
  3. temperatureThereafter, the reactor was cooled to room temperature

Sources & evidence

ORD record
ord-174812cc3a8b4c44ba7d4009f47fe7a8
Source dataset
uspto-grants-1988_06
Patent number
US04749786

Reaction notes

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