Sodium hydride → HCID 178448058, compound

HRID 1264460Notes

Reaction equation

HRID 1264460 reaction equation
[H-].[Na+].C(P([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])CC)C.[H][H].[CH2:16]([C@H:19]1[CH2:24][CH2:23][C@H:22]([C@H:25]2[CH2:30][CH2:29][C@H:28]([CH:31]=O)[CH2:27][CH2:26]2)[CH2:21][CH2:20]1)[CH2:17][CH3:18]>C1COCC1.O>[CH2:16]([C@H:19]1[CH2:24][CH2:23][C@H:22]([C@H:25]2[CH2:26][CH2:27][C@H:28]([CH:31]=[CH:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:29][CH2:30]2)[CH2:21][CH2:20]1)[CH2:17][CH3:18]

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 11788582Ethyl diethylphosphinoacetateHCID 178418361HCID 178418361, compoundHCID 178448068HCID 178448068, compound

Product 1

HCID 178448058HCID 178448058, compoundYield 46.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
-5 °C

Procedure

In a flask equipped with a stirrer, a thermometer and a dropping funnel, 3.36 g of sodium hydride was dissolved in 50 ml of THF under nitrogen atmosphere and the solution was cooled down to −5° C. with stirring. 30 ml of a THF solution of ethyl diethylphosphinoacetate (18.8 g) was added dropwise thereto, and the solution was further stirred for 2 hours. After observing hydrogen gas generation, 50 ml of a THF solution of trans-4-(trans-4-propylcyclohexyl)-cyclohexanecarbaldehyde (16.5 g) was added dropwise. Further, the solution was warmed to room temperature and stirred for 3 hours. After stirring, water was added to the reaction mixture and extracted with toluene (50 ml×3). The organic layer was washed with water, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure to obtain 10.0 g of ethyl 3-(trans-4-(trans-4-propylcyclohexyl)cyclohexyl)propenoate.

Workup

  1. customIn a flask equipped with a stirrer
  2. stirringthe solution was further stirred for 2 hours
  3. additionwas added dropwise
  4. temperatureFurther, the solution was warmed to room temperature
  5. stirringstirred for 3 hours
  6. stirringAfter stirring
  7. extractionextracted with toluene (50 ml×3)
  8. washThe organic layer was washed with water
  9. dry with materialdried over anhydrous magnesium sulfate
  10. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a5528146f7034c4eaf621914d906d00b
Source dataset
uspto-grants-2003_04
Patent number
US06544604B2

Reaction notes

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