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Dimethylformamide → Benzyl 3-(4-pyridyl)-2-butenoate

HRID 18390
Notes
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Reaction equation

HRID 18390 reaction equation
[CH3:1]N(C)C=O.[C:6]([C:9]1[CH:14]=[CH:13][N:12]=[CH:11][CH:10]=1)(=O)[CH3:7].[Br-].[CH2:16]([O:23][C:24]([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=[O:25])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(=O)([O-])[O-].[K+].[K+]>C(OCC)C>[N:12]1[CH:13]=[CH:14][C:9]([C:6]([CH3:1])=[CH:7][C:24]([O:23][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:25])=[CH:10][CH:11]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 142824-AcetylpyridineHCID 23024669(Benzyloxycarbonyl)triphenylphosphonium bromide

Product 1

HCID 67118931Benzyl 3-(4-pyridyl)-2-butenoateYield 42%

Reagents, catalysts & solvents 1

HCID 3283
Diethyl Ether
Solvent

Procedure

N,N-Dimethylformamide (33 ml) was added to a mixture of 4-acetylpyridine (2.00 g, 16.5 mmol) and (benzyloxycarbonyl)triphenylphosphonium bromide (8.94 g, 18.2 mmol), and the whole was stirred under ice-cooling. Potassium carbonate (9.12 g, 66.0 mmol) was added thereto, and the whole was stirred at an external temperature of 70° C. overnight. The reaction mixture was diluted with diethyl ether (100 ml), and the whole was washed with water (100 ml, twice) and saturated brine (50 ml) successively. The organic layer was dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give benzyl 3-(4-pyridyl)-2-butenate (1.77 g, 42%: mixture of E body and Z body) as a pale yellow oily matter.

Workup

  1. temperaturecooling
  2. stirringthe whole was stirred at an external temperature of 70° C. overnight
  3. washthe whole was washed with water (100 ml
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-eae2e1c8cc89488595a923339b143a1c
Source dataset
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07741346B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes