Methanol → AC-Pro-ome

HRID 579828

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

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, 0.75 mmol of CH3OH, 56.8 mg of (PPh3)2PdCl2, and 72.35 mg of N-acetyl-2-pyrroline. The reactor was pressurized with 1000 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 100% conversion of N-acetyl-2-pyrroline and 25.2% yield of N-acetylproline methyl ester.

Workup

customA 70 mL stainless steel high pressure reactor having
customwas pressurized with 1000 psi of CO and 300 psi of H2 at room temperature
temperatureThereafter, the reactor was cooled to room temperature

Sources & evidence

ORD record: ord-393971dd9a944e91b90cd4b696449cac
Source dataset: uspto-grants-1988_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04749786

Linked notes

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