Ethanol → HCID 57771539, compound

HRID 2070569Notes

Reaction equation

HRID 2070569 reaction equation
[CH2:1]1[C:5]2([CH2:10][CH2:9][C:8]([C:11]#N)=[CH:7][CH2:6]2)[CH2:4][CH2:3][CH2:2]1.S(=O)(=O)(O)O.[OH2:18].[CH2:19]([OH:21])[CH3:20]>>[CH2:19]([O:21][C:11]([C:8]1[CH2:9][CH2:10][C:5]2([CH2:4][CH2:3][CH2:2][CH2:1]2)[CH2:6][CH:7]=1)=[O:18])[CH3:20]

Participants

5

Reactant 4

HCID 702EthanolHCID 962WaterHCID 1118Sulfuric AcidHCID 57771421HCID 57771421, compound

Product 1

HCID 57771539HCID 57771539, compound

Procedure

To a solution of spiro[4.5]dec-7-ene-8-carbonitrile (2.8 g) obtained in Step 2 in ethanol (30 mL) was added concentrated sulfuric acid (3 mL), followed by heating the reaction mixture under reflux while stirring for 5 days. After cooling down to room temperature and adding water, the reaction mixture was extracted with ethyl acetate twice. The organic layer was washed successively with saturated aqueous sodium bicarbonate solution and saturated brine, dried and concentrated. The residue was purified by column chromatography on silica gel (ethyl acetate:hexane (volume ratio)=1:4) to give spiro[4.5]dec-7-ene-8-carboxylic acid ethyl ester (2.8 g).

Workup

  1. temperatureby heating the reaction mixture
  2. temperatureunder reflux
  3. extractionthe reaction mixture was extracted with ethyl acetate twice
  4. washThe organic layer was washed successively with saturated aqueous sodium bicarbonate solution and saturated brine
  5. customdried
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography on silica gel (ethyl acetate:hexane (volume ratio)=1:4)

Sources & evidence

ORD record
ord-b20f6c8199204f0c9c8a6a3e2e7f4749
Source dataset
uspto-grants-2012_10
Patent number
US08299296B2

Reaction notes

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