Methanol → AC-Pro-ome

HRID 579827

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

Reactant 4

HCID 887Methanol

HCID 8028Tetrahydrofuran

HCID 12391Pentadecane

HCID 10909522N-Acetyl-2-pyrroline2×

Product 1

HCID 11019314AC-Pro-omeYield 4.1%

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, 10.0 mg of Co2 (CO)6 (PPh3)2, and 55.0 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 was stirred at 100° C. for 21.75 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 76.6% conversion of N-acetyl-2-pyrroline and 4.1% yield of N-acetylproline methyl ester.

Workup

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

Sources & evidence

ORD record: ord-2e52c745d8674c228c63de238422aa25
Source dataset: uspto-grants-1988_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04749786

Linked notes

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