Diethyl Malonate → HCID 69557395, compound

HRID 427412Notes

Reaction equation

HRID 427412 reaction equation
[C:1]([O:9][CH2:10][CH3:11])(=[O:8])[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].[Na].[C:13]1([C:19]2(S([O-])(=O)=O)[CH:24]=[CH:23][C:22]([CH3:25])=[C:21](CC3CCCCC3)[CH2:20]2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>CCO>[CH2:10]([O:9][C:1](=[O:8])[CH:2]([CH2:25][CH:22]1[CH2:21][CH2:20][CH:19]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH2:24][CH2:23]1)[C:3]([O:5][CH2:6][CH3:7])=[O:4])[CH3:11]

Participants

5

Reactant 3

HCID 7761Diethyl MalonateHCID 5360545SodiumHCID 131722962HCID 131722962, compound

Product 1

HCID 69557395HCID 69557395, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Diethyl malonate (3.1 g, 19.7 mmol, 1.5 equiv) was added dropwise to a solution of sodium (1.25 g, 54.0 mmol, 4.0 equiv) in EtOH (50 mL). 4-Phenyl-cyclohexylmethyl-p-toluene sulfonate (˜13.1 mmol, ˜1.0 equiv, the crude product from the previous step) was added as a solution in 50 mL of EtOH. The resulting mixture was refluxed for 8 h. The reaction mixture was cooled and evaporated to dryness and then dissolved in water (150 mL) and the crude product extracted with 3×100 mL EtOAc. The organic layer was dried over MgSO4, filtered and concentrated. The crude product was purified by flash chromatography on SiO2 using 10% EtOAc in hexanes to give the desired product as a colorless oil (2.79 g).

Workup

  1. temperatureThe resulting mixture was refluxed for 8 h
  2. temperatureThe reaction mixture was cooled
  3. customevaporated to dryness
  4. dissolutiondissolved in water (150 mL)
  5. extractionthe crude product extracted with 3×100 mL EtOAc
  6. dry with materialThe organic layer was dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe crude product was purified by flash chromatography on SiO2 using 10% EtOAc in hexanes

Sources & evidence

ORD record
ord-b206d435a0184ac3b1ede0a72a774361
Source dataset
uspto-grants-2001_11
Patent number
US06313117B1

Reaction notes

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