Hydrochloric Acid → Methyl 5-cyano-5-(4-fluorophenyl)-2-oxocyclohexanecarboxylate

HRID 2370291Notes

Reaction equation

[C:1](OC)(=[O:4])[CH:2]=[CH2:3].[F:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][C:15]#[N:16])=[CH:10][CH:9]=1.C[O-:18].[Na+].Cl.[CH2:21]1[CH2:25][O:24][CH2:23][CH2:22]1>CO>[CH3:23][O:24][C:25]([CH:21]1[CH2:22][C:14]([C:15]#[N:16])([C:11]2[CH:12]=[CH:13][C:8]([F:7])=[CH:9][CH:10]=2)[CH2:3][CH2:2][C:1]1=[O:4])=[O:18]

Participants

Conditions

Temperature: 50 °C

Procedure

70 mL of methyl acrylate and 44.4 mL of 4-fluorophenylacetonitrile were dissolved in 200 mL of THF and 50 mL of methanol. 150 mL of a 30% solution of sodium methylate in methanol were added slowly. The mixture was stirred at room temperature for 15 h and for 4 h at 50° C. The mixture was cooled to room temperature and poured onto cooled 2N HCl. The aqueous layer was washed with ethyl acetate three times, the combined organic layers were extracted with water and brine, dried over sodium sulfate and evaporated to dryness to give 101.5 g of crude product, that was sufficiently pure for further conversion. Rt=1.60 min (Method C). Detected mass: 276.2 (M+H+).

Workup

temperatureThe mixture was cooled to room temperature
additionpoured
washThe aqueous layer was washed with ethyl acetate three times
extractionthe combined organic layers were extracted with water and brine
dry with materialdried over sodium sulfate
customevaporated to dryness

Sources & evidence

ORD record: ord-67e7e7c1d6be423b9846ac128de1205f
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08710077B2

Reaction notes

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