HCID 67995940, compound → HCID 67995749, compound

HRID 1615137Notes

Reaction equation

HRID 1615137 reaction equation
C(OC(=O)CC([C:9]1([CH2:22][CH:23]=[CH2:24])[CH2:21][CH2:20][C:12]2([O:17][CH2:16][C:15]([CH3:19])([CH3:18])[CH2:14][O:13]2)[CH2:11][CH2:10]1)C#N)C>[OH-].[K+].C(O)CO.O.C(O)(=O)C>[CH2:22]([C:9]1([CH2:11][C:12]([OH:17])=[O:13])[CH2:21][CH2:20][C:12]2([O:17][CH2:16][C:15]([CH3:19])([CH3:18])[CH2:14][O:13]2)[CH2:11][CH2:10]1)[CH:23]=[CH2:24]

Participants

6

Reactant 1

HCID 67995940HCID 67995940, compound

Product 1

HCID 67995749HCID 67995749, compound

Reagents, catalysts & solvents 4

HCID 174Ethylene GlycolSolventHCID 176Acetic AcidSolventHCID 962WaterSolventHCID 14797Potassium HydroxideSolvent

Conditions

Temperature
190 °C

Procedure

3-(9-Allyl-3,3-dimethyl-1,5-dioxa-spiro[5.5]undec-9-yl)-3-cyano-propionic acid ethyl ester (4.21 g) is dissolved in a solution of KOH (16.5 g) in ethylene glycol (110 mL) and the resulting mixture is heated to 190° C. and stirred at this temperature for 3 h. After cooling to room temperature, the solution is diluted with water and neutralized with acetic acid. The resulting solution is extracted several times with ethyl acetate. The extracts are combined and the solvent is evaporated. The residue is chromatographed on silica gel (cyclohexane/ethyl acetate 1:0→1:1) to give the title compound. Yield: 3.54 g (quantitative); Mass spectrum (ESI+): m/z=283 [M+H]+.

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionThe resulting solution is extracted several times with ethyl acetate
  3. customthe solvent is evaporated
  4. customThe residue is chromatographed on silica gel (cyclohexane/ethyl acetate 1:0→1:1)

Sources & evidence

ORD record
ord-cbe6846a191344e7aefd104145c799f6
Source dataset
uspto-grants-2014_07
Patent number
US08765744B2

Reaction notes

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