Sodium ethoxide → HCID 20520589, compound

HRID 223718Notes

Reaction equation

CC[O-].[Na+].[Na].[SH:6][C:7]1[CH:8]=[C:9]([CH:13]([CH3:19])[C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:10]=[CH:11][CH:12]=1.Cl[CH2:21][C@@H:22]1[CH2:27][CH2:26][CH2:25][CH2:24][C@H:23]1[C:28]#[N:29]>C(O)C>[C:28]([CH:23]1[CH2:24][CH2:25][CH2:26][CH2:27][CH:22]1[CH2:21][S:6][C:7]1[CH:8]=[C:9]([CH:13]([CH3:19])[C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:10]=[CH:11][CH:12]=1)#[N:29]

Participants

Conditions

Temperature: 100 °C

Procedure

Sodium ethylate prepared from sodium (0.23 g) and ethanol (10 ml) was added to ethyl 2-(3-mercaptophenyl)propionate (2.10 g) and the mixture was stirred for a while. Thereto was added trans-2-(chloromethyl)cyclohexanenitrile (1.58 g) and the resulting mixture was refluxed for 5 hours in an oil bath maintained at 100° C. The reaction mixture was evaporated to dryness under reduced pressure and to the residue was added toluene. After removal of the insoluble material by filtration, the solvent was distilled off under reduced pressure. The residue was chromatographed on silica gel, using chloroform as an eluent, to give ethyl 2-[3-(2-cyanocyclohexylmethylthio)phenyl]propionate (2.6 g) as an oil. IRνmaxfilm cm-1 : 2230 (C≡N), 1720 (C=O). MS m/e: 331 (M+).

Workup

temperaturethe resulting mixture was refluxed for 5 hours in an oil bath
customThe reaction mixture was evaporated to dryness under reduced pressure and to the residue
additionwas added toluene
customAfter removal of the insoluble material
filtrationby filtration
distillationthe solvent was distilled off under reduced pressure
customThe residue was chromatographed on silica gel

Sources & evidence

ORD record: ord-8ac279c7c02c4b319240ca6387d18c1a
Source dataset: uspto-grants-1982_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04356186

Reaction notes

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