(Triphenylphosphoranylidene)acetaldehyde → HCID 56607884, compound

HRID 1164886Notes

Reaction equation

HRID 1164886 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH:14]=O)[CH2:10][CH:9]1[C:16]([O:18][CH2:19][CH3:20])=[O:17])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH:21]([CH:23]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=[O:22]>C1(C)C=CC=CC=1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH:14]=[CH:23][CH:21]=[O:22])[CH2:10][CH:9]1[C:16]([O:18][CH2:19][CH3:20])=[O:17])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 75051(Triphenylphosphoranylidene)acetaldehydeHCID 14541450HCID 14541450, compound

Product 1

HCID 56607884HCID 56607884, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 1 g of 1-(tert-butoxycarbonyl)-2-ethoxycarbonylpiperidine-4-carboxaldehyde and 2g of formylmethylene-triphenylphosphoran in 16 ml of toluene is heated to 100° (bath) for 2 hours. The solution is cooled and purified by flash chromatography using ethyl acetate/hexane (25:75) to yield 1-(tert-butoxycarbonyl)-2-ethoxycarbonyl-piperidine-4-acrylaldehyde.

Workup

  1. temperatureThe solution is cooled
  2. custompurified by flash chromatography

Sources & evidence

ORD record
ord-40c560fb72c64330a6527e327bf18c82
Source dataset
uspto-grants-1990_03
Patent number
US04906621

Reaction notes

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