Diethyl Ether → HCID 15661748, compound

HRID 1756336Notes

Reaction equation

HRID 1756336 reaction equation
[CH3:1][CH2:2][O:3][C:4](/[C:6](/P(OCC)(OCC)=O)=[CH:7]\[CH3:8])=[O:5].[K].C([O-])(C)(C)C.[Br:23][C:24]1[N:29]=[C:28]([CH:30]=O)[CH:27]=[CH:26][CH:25]=1.C(OCC)C>O1CCCC1>[CH2:2]([O:3][C:4](=[O:5])/[CH:6]=[CH:7]/[CH:8]=[CH:30]/[C:28]1[CH:27]=[CH:26][CH:25]=[C:24]([Br:23])[N:29]=1)[CH3:1]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 27570096-Bromopyridine-2-carbaldehydeHCID 6272114HCID 6272114, compoundHCID 50987170Potassium tertbutoxide

Product 1

HCID 15661748HCID 15661748, compoundYield 67.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-20 °C

Procedure

A solution of 5.88 g of 4-phosphonocrotonic acid triethyl ester in 60 ml of tetrahydrofuran is mixed in portions with 2.5 g of potassium-tert-butanolate with stirring and under argon atmosphere at -20° C. After 30 minutes, a solution of 2.6 g of 6-bromopyridine-2-aldehyde is instilled at -20° C. and the mixture is stirred at this temperature for another hour. The reaction mixture is poured on ice, shaken out with diethyl ether, the organic phase is washed with saturated common salt solution, dried on sodium sulfate and concentrated by evaporation. The residue is chromatographed on silica gel with hexane/ethyl acetate=95/5. 2.66 g of 5-(6-bromo-2-pyridyl)-(E,E)-2,4-pentadienoic acid ethyl ester is obtained as crude product.

Workup

  1. customis instilled at -20° C.
  2. stirringthe mixture is stirred at this temperature for another hour
  3. additionThe reaction mixture is poured on ice
  4. washthe organic phase is washed with saturated common salt solution
  5. customdried on sodium sulfate
  6. concentrationconcentrated by evaporation
  7. customThe residue is chromatographed on silica gel with hexane/ethyl acetate=95/5

Sources & evidence

ORD record
ord-bd487b9b6f524707ab728848a76d9ab2
Source dataset
uspto-grants-1995_08
Patent number
US05440044

Reaction notes

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