Sodium hydride → HCID 54044169, compound

HRID 1646249Notes

Reaction equation

HRID 1646249 reaction equation
[H-].[Na+].C(OP([CH2:11][C:12]([N:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH:15]1[CH2:20][CH3:21])=[O:13])(OCC)=O)C.[CH3:22][C:23]1[C:24]2[N:25]([N:29]=[C:30]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[C:31]=2[CH:32]=O)[CH:26]=[CH:27][CH:28]=1>O1CCCC1>[CH3:22][C:23]1[C:24]2[N:25]([N:29]=[C:30]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[C:31]=2[CH:32]=[CH:11][C:12]([N:14]2[CH2:19][CH2:18][CH2:17][CH2:16][CH:15]2[CH2:20][CH3:21])=[O:13])[CH:26]=[CH:27][CH:28]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 19092389HCID 19092389, compoundHCID 19092432HCID 19092432, compound

Product 1

HCID 54044169HCID 54044169, compoundYield 99.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Sodium hydride (60%, 110mg) was added to a solution of 1-(2-diethoxyphosphorylacetyl)-2-ethylpiperidine (0.80 g) in tetrahydrofuran (5 ml) at 7° C. under nitrogen atmosphere. A solution of 4-methyl-2-phenylpyrazolo[1,5-a]pyridine-3-carbaldehyde (0.50 g) in tetrahydrofuran (5 ml) was added dropwise to the above solution at 10° C., and then stirred at room temperature for 1 hour. After evaporating the solvent, in vacuo saturated sodium chloride aqueous solution (20 ml) was added to the residue and extracted with ethyl acetate (20 ml×2). Combined extracts were washed with saturated sodium chloride aqueous solution (20 ml), dried over magnesium sulfate and evaporated in vacuo. The residue was chromatographed on silica gel (20 g) with chloroform as an eluent. The fractions containing the objective compound were combined and evaporated in vacuo to give 1-[3-(4-methyl-2-phenylpyrazolo[1,5-a]pyridin-3-yl)acryloyl]-2-ethylpiperidine (trans isomer) (788 mg) as an oil.

Workup

  1. customAfter evaporating the solvent
  2. additionin vacuo saturated sodium chloride aqueous solution (20 ml) was added to the residue
  3. extractionextracted with ethyl acetate (20 ml×2)
  4. washCombined extracts were washed with saturated sodium chloride aqueous solution (20 ml)
  5. dry with materialdried over magnesium sulfate
  6. customevaporated in vacuo
  7. customThe residue was chromatographed on silica gel (20 g) with chloroform as an eluent
  8. additionThe fractions containing the objective compound
  9. customevaporated in vacuo

Sources & evidence

ORD record
ord-713a1bcfc98e47fe9d1d101690a17709
Source dataset
uspto-grants-1993_01
Patent number
US05179103

Reaction notes

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