Sodium Bicarbonate → 4-pyridin-3-ylbutanal

HRID 53566Notes

Reaction equation

HRID 53566 reaction equation
[O:1]1CCCO[CH:2]1[CH2:7][CH2:8][CH2:9][C:10]1[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=1.C([O-])(O)=O.[Na+]>C1COCC1.Cl>[CH:14]1[CH:13]=[N:12][CH:11]=[C:10]([CH2:9][CH2:8][CH2:7][CH:2]=[O:1])[CH:15]=1

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 196941351-(1,3-Dioxan-2-yl)-3-(3-pyridyl)propane

Product 1

HCID 110190264-pyridin-3-ylbutanalYield 94.5%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1.5 g (7.8 mmol) of acetal 157 in 10.0 mL of THF and 10.0 mL of 4N HCl was stirred overnight at room temperature and was then neutralized by the slow addition of solid NaHCO3. The reaction mixture was extracted with ethyl acetate, dried over MgSO4 and concentrated to yield 1.1 g of the aldehyde 158. 1H NMR consistent with structure.

Workup

  1. extractionThe reaction mixture was extracted with ethyl acetate
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-953dc2f4bfb341eeba85ea120230ee5d
Source dataset
uspto-grants-1997_04
Patent number
US05620971

Reaction notes

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