Ethyl 2-methyl-4-oxocyclopent-2-ene-1-carboxylate → Ethyl 2-methyl-4-oxocyclopentanecarboxylate

HRID 2204567Notes

Reaction equation

[CH3:1][C:2]1[CH:3]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:4][C:5](=[O:7])[CH:6]=1>[Pd].CCOC(C)=O>[CH3:1][CH:2]1[CH2:6][C:5](=[O:7])[CH2:4][CH:3]1[C:8]([O:10][CH2:11][CH3:12])=[O:9]

Participants

Conditions

Temperature: 0 °C

Procedure

A round-bottom flask was charged with 10% palladium on carbon (7.6 g, 7.1 mmol). The flask was cooled to about 0° C. and EtOAc (580 mL) was added under a nitrogen atmosphere. The cooling bath was removed and ethyl 2-methyl-4-oxocyclopent-2-enecarboxylate (60.0 g, 357 mmol) was added. Hydrogen gas was bubbled through the mixture for about 5 min and the mixture was then stirred under a hydrogen atmosphere (1 atmosphere) for about 48 h. The hydrogen source was removed and the mixture was bubbled with nitrogen for about 5 min and was filtered through a pad of Celite®. The filter cake was rinsed with EtOAc (500 mL). The filtrate was concentrated under reduced pressure to give ethyl 2-methyl-4-oxocyclopentanecarboxylate (59.9 g, 99%) as a yellow liquid: 1H NMR (CDCl3) δ 4.23-4.14 (m, 2H), 3.18 (ddd, J=5.6, 6.8, 8.1 Hz, 1H), 2.73-2.65 (m, 1H), 2.60 (ddd, J=1.7, 5.5, 18.7 Hz, 1H), 2.42-2.29 (m, 2H), 2.15 (ddd, J=1.7, 7.9, 18.3 Hz, 1H), 1.29 (t, J=7.1 Hz, 3H), 1.07 (d, J=7.0 Hz, 3H).

Workup

customThe cooling bath was removed
customHydrogen gas was bubbled through the mixture for about 5 min
customThe hydrogen source was removed
customthe mixture was bubbled with nitrogen for about 5 min
filtrationwas filtered through a pad of Celite®
washThe filter cake was rinsed with EtOAc (500 mL)
concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record: ord-385943b537fb433e93f48b088a4704e4
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09365579B2

Reaction notes

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