HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Sodium ethoxide → HCID 20520589, compound

HRID 223718
Notes
Print preview

Reaction equation

HRID 223718 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 2723922Sodium ethoxideHCID 5360545SodiumHCID 12832492HCID 12832492, compoundHCID 12832494(1R,2R)-2-(Chloromethyl)cyclohexane-1-carbonitrile

Product 1

HCID 20520589HCID 20520589, compoundYield 78.5%

Reagents, catalysts & solvents 1

HCID 702
Ethanol
Solvent

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

  1. temperaturethe resulting mixture was refluxed for 5 hours in an oil bath
  2. customThe reaction mixture was evaporated to dryness under reduced pressure and to the residue
  3. additionwas added toluene
  4. customAfter removal of the insoluble material
  5. filtrationby filtration
  6. distillationthe solvent was distilled off under reduced pressure
  7. 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

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes