Tetrahydrofuran → HCID 67345946, compound

HRID 383767Notes

Reaction equation

HRID 383767 reaction equation
[H-].[Na+].C[C:4](P(OC)(O)=O)([C:6]([O-:8])=[O:7])C.[N:14]1[CH:19]=[CH:18][CH:17]=[C:16]([C:20](=O)[CH3:21])[CH:15]=1.[CH2:23]1COCC1>>[N:14]1[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([CH3:21])=[CH:4][C:6]([O:8][CH3:23])=[O:7])[CH:15]=1

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 95893-AcetylpyridineHCID 24758Sodium hydrideHCID 53413272Trimethylphosphonoacetate

Product 1

HCID 67345946HCID 67345946, compound

Procedure

Sodium hydride (192 mg of a 60% wt. suspension, 4.80 mmol) was added in several portions to a stirred solution of trimethylphosphonoacetate (712 μL, 4.40 mmol) in THF (20.0 mL). After 5 min, 1-pyridin-3-ylethanone (440 μL, 4.00 mmol) was added dropwise, and the resulting mixture was heated to reflux. After 20 h, the reaction mixture was cooled to rt, poured into said. aq. NH4Cl and extracted with EtOAc. The combined organics were washed with brine, dried (sodium sulfate) and concentrated in vacuo. Purification of the crude residue by flash chromatography on silica gel (gradient elution; 0%-60% EtOAc/hexanes as eluent) afforded the title compound i-8a as a separable mixture of two isomers. m/z (ES) 178 (MH)+.

Workup

  1. temperaturethe resulting mixture was heated to reflux
  2. waitAfter 20 h
  3. additionpoured
  4. extractionaq. NH4Cl and extracted with EtOAc
  5. washThe combined organics were washed with brine
  6. dry with materialdried (sodium sulfate)
  7. concentrationconcentrated in vacuo
  8. customPurification of the crude residue by flash chromatography on silica gel (gradient elution; 0%-60% EtOAc/hexanes as eluent)

Sources & evidence

ORD record
ord-d9db0197147f4463b44575f3f8da284b
Source dataset
uspto-grants-2013_02
Patent number
US08367679B2

Reaction notes

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