Hydrochloric Acid → 3-(3-Methylfuran-2-yl)-3-oxopropanenitrile

HRID 1355883Notes

Reaction equation

[C:1](#[N:3])[CH3:2].C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[CH3:14][C:15]1[CH:19]=[CH:18][O:17][C:16]=1[C:20](OC)=[O:21].Cl>C1COCC1>[CH3:14][C:15]1[CH:19]=[CH:18][O:17][C:16]=1[C:20](=[O:21])[CH2:2][C:1]#[N:3]

Participants

Conditions

Temperature: -20 °C

Procedure

Following the method of Turner and Jacks (J. Org. Chem. 1989, 54, 4229), to a stirred solution of 9.4 ml (179 mmol) acetonitrile in 250 ml dry THF under argon at −78° C. was added dropwise 78.9 ml (78.9 mmol) lithium bis(trimethylsilyl)amide solution (1M in THF) and stirring continued for 30 minutes, after which a solution of 5.0 g (35.7 mmol) methyl 3-methyl-2-furoate in 20 ml THF was added dropwise and stirring continued while the reaction mixture was allowed to warm slowly to −20° C. The reaction mixture was then cannulated into a rapidly stirred solution of 1M hydrochloric acid at 0° C. The mixtured was extracted twice with ether and the combined organic phases dried over sodium sulfate and concentrated in vacuo. Chromatography (ethyl acetate/hexane 1/4) afforded 4.43 g (83%) 3-(3-methyl-furan-2-yl)-3-oxo-propionitrile as a yellow crystalline solid. EI-MS m/e (%): 149 (M+, 20), 109 ([M—CH2CN]+, 100).

Workup

stirringstirring
extractionThe mixtured was extracted twice with ether
dry with materialthe combined organic phases dried over sodium sulfate
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-9167a8d7b6bd4bf89d16504422fcaea8
Source dataset: uspto-grants-2003_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06586441B2

Reaction notes

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