Ethyl Acetate → HCID 54442297, compound

HRID 1386808Notes

Reaction equation

HRID 1386808 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([CH:14]=O)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:16][CH2:17][O:18][C:19]([CH3:21])=[O:20]>C1COCC1>[CH2:1]([N:8]1[CH2:9][CH2:10][CH:11]([CH:14]=[CH:21][C:19]([O:18][CH2:17][CH3:16])=[O:20])[CH2:12][CH2:13]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 8857Ethyl AcetateHCID 895841-Benzylpiperidine-4-carbaldehyde

Product 1

HCID 54442297HCID 54442297, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 15.5 mL of 1 M sodium bis(triemthylislyl)amide in 20 ml of THF was added 2.8 g triethyl phosphonoacetate at 0° C., and stirred at 0° C. for 15 min. After the addition of 1-benzyl-piperidine-4-carbaldehyde (from Example 162, step A) in 10 mL of 1BF, the reaction was stirred at 0° C. for 15 min. The reaction was warmed up to rt and stirred for 14 hr. The mixture was diluted with 35 ml of EtOAc and washed with H2O. Aqueous phase was extracted with 2×30 mL EtOAc. The combined organic phases were washed with brine and dried over MgSO4. Concentration gave a 2.43 g of title compound as a viscous oil.

Workup

  1. stirringthe reaction was stirred at 0° C. for 15 min
  2. temperatureThe reaction was warmed up to rt
  3. stirringstirred for 14 hr
  4. washwashed with H2O
  5. extractionAqueous phase was extracted with 2×30 mL EtOAc
  6. washThe combined organic phases were washed with brine
  7. dry with materialdried over MgSO4
  8. concentrationConcentration

Sources & evidence

ORD record
ord-4056ad5b79464a18adf0901e5e3be93f
Source dataset
uspto-grants-2001_07
Patent number
US06265434B1

Reaction notes

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