Methanol → AC-Pro-ome

HRID 579831

Reaction equation

HRID 579831 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 1.1%

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, 4.88 mg of Fe(CO)5, and 57.19 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 21 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 86.7% conversion of N-acetyl-2-pyrroline and 1.1% 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-4d8e1cb8d2074a76818758a2f5464a3c
Source dataset
uspto-grants-1988_06
Patent number
US04749786

Linked notes

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