Water → HCID 59658097, compound

HRID 2055735Notes

Reaction equation

HRID 2055735 reaction equation
C(OC([CH:6]1[CH2:11][C:10]([C:17]#[N:18])([C:12]2[CH:16]=[CH:15][S:14][CH:13]=2)[CH2:9][CH2:8][C:7]1=[O:19])=O)C.O.[OH-].[Na+]>Cl.C(O)(=O)C>[O:19]=[C:7]1[CH2:8][CH2:9][C:10]([C:12]2[CH:16]=[CH:15][S:14][CH:13]=2)([C:17]#[N:18])[CH2:11][CH2:6]1

Participants

6

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 69207476HCID 69207476, compound

Product 1

HCID 59658097HCID 59658097, compoundYield 43.5%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 313Hydrochloric AcidSolvent

Procedure

5-cyano-2-oxo-5-thiophen-3-yl-cyclohexanecarboxylic acid ethylester (40 g; 0.14 mole) dissolved in a mixture of concentrated hydrochloric acid (200 ml) and glacial acetic acid (400 ml) was heated with stirring for about 4 hours to reflux. On completion of the reaction (reaction monitored by thin layer chromatography), water (100 ml) was added and neutralized with aqueous sodium hydroxide solution (200 ml) and extracted with ethylacetate (2×400 ml). The organic phase was washed with sodium hydrogen carbonate solution (200 ml) and water (100 ml), dried (sodium sulfate) and concentrated under vacuum. Purification by column chromatography (silica gel, 25% ethylacetate in n-hexane) yielded 12.5 g 4-oxo-1-thiophen-3-yl-cyclohexanecarbonitrile (42%; pale yellow solid).

Workup

  1. temperaturewas heated
  2. temperatureto reflux
  3. additionwas added
  4. extractionextracted with ethylacetate (2×400 ml)
  5. washThe organic phase was washed with sodium hydrogen carbonate solution (200 ml) and water (100 ml)
  6. dry with materialdried (sodium sulfate)
  7. concentrationconcentrated under vacuum
  8. customPurification by column chromatography (silica gel, 25% ethylacetate in n-hexane)

Sources & evidence

ORD record
ord-caf63a3b981346edbb1b2052154c4e58
Source dataset
uspto-grants-2008_02
Patent number
US07332519B2

Reaction notes

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