Triethyl phosphonoacetate → HCID 67231669, compound

HRID 2047458Notes

Reaction equation

HRID 2047458 reaction equation
[H-].[Na+].C(OP([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])(OCC)=O)C.[F:17][C:18]1[CH:19]=[CH:20][C:21]([CH:24]=O)=[N:22][CH:23]=1>C1COCC1.O>[F:17][C:18]1[CH:19]=[CH:20][C:21](/[CH:24]=[CH:11]/[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[N:22][CH:23]=1

Participants

6

Reactant 3

HCID 13345Triethyl phosphonoacetateHCID 24758Sodium hydrideHCID 103516975-Fluoropyridine-2-carboxaldehyde

Product 1

HCID 67231669HCID 67231669, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of sodium hydride (55 wt %, 1.97 g) in THF (200 ml) was added at 0° C. ethyl (diethoxyphosphoryl)acetate (9.3 g), and the mixture was stirred at 30 min. To this mixture was added a solution of the compound (4.7 g) obtained in step 1 in THF (200 mL) at 0° C., and the mixture was stirred at room temperature for 12 hr. The mixture was diluted with water (500 mL), extracted with ethyl acetate (500 mL), dried and concentrated under reduced pressure. The residue was separated and purified by silica gel column chromatography (25% ethyl acetate/hexane) to give ethyl (2E)-3-(5-fluoropyridin-2-yl)prop-2-enoate (6.2 g, 85%) as a white powder.

Workup

  1. stirringthe mixture was stirred at room temperature for 12 hr
  2. extractionextracted with ethyl acetate (500 mL)
  3. customdried
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was separated
  6. custompurified by silica gel column chromatography (25% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-567cb37c00de4e489d7b26e6f1cf0d7d
Source dataset
uspto-grants-2013_11
Patent number
US08592454B2

Reaction notes

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