Water → HCID 178444503, compound

HRID 1264458Notes

Reaction equation

HRID 1264458 reaction equation
C(P([CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8])CC)C.CC(C)([O-])C.[K+].[CH2:18]([C@H:23]1[CH2:28][CH2:27][C@H:26]([C@H:29]2[CH2:34][CH2:33][C@H:32]([CH:35]=O)[CH2:31][CH2:30]2)[CH2:25][CH2:24]1)[CH2:19][CH2:20][CH2:21][CH3:22].O>O1CCCC1.C1(C)C=CC=CC=1>[CH2:18]([C@H:23]1[CH2:28][CH2:27][C@H:26]([C@H:29]2[CH2:34][CH2:33][C@H:32]([CH:35]=[CH:6][C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH2:31][CH2:30]2)[CH2:25][CH2:24]1)[CH2:19][CH2:20][CH2:21][CH3:22]

Participants

7

Reactant 4

HCID 962WaterHCID 11788582Ethyl diethylphosphinoacetateHCID 23665647Potassium tert-butoxideHCID 178444507HCID 178444507, compound

Product 1

HCID 178444503HCID 178444503, compoundYield 40.5%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
-5 °C

Procedure

In a 1-L three-neck flask equipped with a stirrer, a thermometer and a dropping funnel, 27.6 g (122.9 mmol) of ethyl diethylphosphinoacetate was dissolved in 350 ml of IRAQ tetrahydrofuran (hereinafter abbreviated as THF) under nitrogen atmosphere and the solution was cooled down to −5° C. while stirring. 15.2 g (135.2 mmol) of potassium t-butoxide was added thereto, and the solution was stirred at room temperature for 2 hours. The solution was cooled down again to 0° C., and a solution of 25.0 g (94.5 mmol) of trans-4-(trans-4-pentylcyclohexyl)cyclohexanecarbaldehyde dissolved in 100 ml of THF was added dropwise. Further, the solution was stirred at room temperature for 14 hours, and then 200 ml of water and 400 ml of toluene were added to the reaction mixture and stirred. The separated toluene layer was washed twice with 200 ml of water and dried over anhydrous magnesium sulfate, and then toluene was distilled off under reduced pressure. The residue was purified by means of a silica gel column chromatography with toluene used as a developing solvent to obtain 12.8 g of ethyl 3-(trans-4-(trans-4-pentylcyclohexyl)cyclohexyl)propenoate (yellow oily substance).

Workup

  1. customIn a 1-L three-neck flask equipped with a stirrer
  2. stirringthe solution was stirred at room temperature for 2 hours
  3. temperatureThe solution was cooled down again to 0° C.
  4. additionwas added dropwise
  5. stirringFurther, the solution was stirred at room temperature for 14 hours
  6. stirringstirred
  7. washThe separated toluene layer was washed twice with 200 ml of water
  8. dry with materialdried over anhydrous magnesium sulfate
  9. distillationtoluene was distilled off under reduced pressure
  10. customThe residue was purified by means of a silica gel column chromatography with toluene

Sources & evidence

ORD record
ord-8dcf2ea773e347af99993038a6a9f8c4
Source dataset
uspto-grants-2003_04
Patent number
US06544604B2

Reaction notes

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