Tetrahydrofuran → HCID 12727115, compound

HRID 2176896Notes

Reaction equation

HRID 2176896 reaction equation
[O:1]=C(CCC)CP(=O)(OCC)OCC.[H-].[Na+].[C:17]([C:20]1[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=1)(=O)[CH3:18].[CH2:26]1[CH2:30][O:29][CH2:28][CH2:27]1>>[N:22]1[CH:23]=[CH:24][CH:25]=[C:20](/[C:17](/[CH3:18])=[CH:27]/[C:28]([O:29][CH2:30][CH3:26])=[O:1])[CH:21]=1

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 95893-AcetylpyridineHCID 24758Sodium hydrideHCID 11127861Phosphonic acid, (2-oxopentyl)-, diethyl ester

Product 1

HCID 12727115HCID 12727115, compoundYield 40%

Procedure

Diethyl 2-oxopentyl-phosphonate (1.85 g, 8.26 mol) was added dropwise to a suspension of sodium hydride (0.50 g, 12.4 mmol, 60%) in dry THF (15 ml) followed by 3-acetyl pyridine (1.00 g, 8.26 mmol) at room temperature. The reaction mixture was stirred for 2 h at room temperature, quenched with acetic acid and was adjusted to pH-6. The reaction mixture was diluted with water and extracted with CHCl3. The combined organic layer was washed with brine, dried over anhydrous sodium sulfate, filtered and evaporated to dryness to yield the crude compound. Purification by column chromatography by means of neutral alumina using 10-15% ethyl acetate in petroleum ether as eluent afforded 600 mg (40%) of (E)-ethyl 3-(pyridin-3-yl)but-2-enoate as colorless liquid.

Workup

  1. customquenched with acetic acid
  2. additionThe reaction mixture was diluted with water
  3. extractionextracted with CHCl3
  4. washThe combined organic layer was washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. customevaporated to dryness
  8. customto yield the crude compound
  9. customPurification by column chromatography by means of neutral alumina using 10-15% ethyl acetate in petroleum ether as eluent

Sources & evidence

ORD record
ord-38606dbd78d0441b86cef11af176338d
Source dataset
uspto-grants-2015_06
Patent number
US09067888B2

Reaction notes

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