Ethyl Acetoacetate → 2-Acetyl-4-cyclohexyl-but-2-enoic acid ethyl ester

HRID 2236184Notes

Reaction equation

HRID 2236184 reaction equation
[CH:1]1([CH2:7][CH:8]=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:10]([O:16][CH2:17][CH3:18])(=[O:15])[CH2:11][C:12]([CH3:14])=[O:13]>C(O)C.CCOCC.N1CCCCC1>[CH2:17]([O:16][C:10](=[O:15])[C:11]([C:12](=[O:13])[CH3:14])=[CH:8][CH2:7][CH:1]1[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1)[CH3:18]

Participants

6

Reactant 2

HCID 8868Ethyl AcetoacetateHCID 3166272-Cyclohexylacetaldehyde

Product 1

HCID 675368842-Acetyl-4-cyclohexyl-but-2-enoic acid ethyl esterYield 109.6%

Reagents, catalysts & solvents 3

HCID 8082PiperidineCatalystHCID 702EthanolSolvent2×HCID 3283Diethyl EtherSolvent

Procedure

A solution of the above cyclohexyl-acetaldehyde (1.04 g, 8.25 mmol) and ethyl acetoacetate (0.873 mL, 6.85 mmol) in 300 mL ethanol was stirred in an ice bath as piperidine (7.3 uL, 73 umol) in 380 uL ethanol was added. The mixture was stirred in the ice bath for 5 hours and placed in a refrigerator for 16 hours. The reaction mixture was diluted with 50 mL ether and extracted with saturated sodium chloride (3×30 mL containing 2 drops AcOH). The brine layers were back-extracted with ether (2×40 mL). The combined ether layers were washed with brine (30 mL), dried over sodium sulfate, filtered and evaporated to give 2-acetyl-4-cyclohexyl-but-2-enoic acid ethyl ester (1.79 g).

Workup

  1. additionwas added
  2. extractionextracted with saturated sodium chloride (3×30 mL containing 2 drops AcOH)
  3. extractionThe brine layers were back-extracted with ether (2×40 mL)
  4. washThe combined ether layers were washed with brine (30 mL)
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-d14b841349014306b2063c879e5f9c41
Source dataset
uspto-grants-2010_05
Patent number
US07714126B2

Reaction notes

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