Diethyl Ether → HCID 10352231, compound

HRID 1064018Notes

Reaction equation

HRID 1064018 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH:7]=O)=[CH:3][CH:2]=1.[OH-:9].[Li+].[CH3:11][CH2:12][O:13][CH2:14][CH3:15]>C1COCC1>[N:1]1[CH:2]=[CH:3][C:4](/[CH:7]=[CH:11]/[C:12]([O:13][CH2:14][CH3:15])=[O:9])=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 3939Lithium HydroxideHCID 133894-Pyridinecarboxaldehyde

Product 1

HCID 10352231HCID 10352231, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-pyridinecarboxaldehyde (67 ml, 700 mmol) and triethyl phosphonacetate (152 ml, 770 mmol) in THF (200 ml) at room temperature was added lithium hydroxide (32.4 g, 770 mmol). After 18 hours ether (500 ml) was added and the solution was washed with sodium hydrogen carbonate, brine and concentrated to give a white solid. Yield 102.1 g (83%). NMR: 8.62 (d, 2H), 7.60 (d, 1H), 7.35 (d, 2H), 6.59 (d, 1H), 4.30 (q, 2H), 1.35 (t, 3H); m/z 178.3.

Workup

  1. washthe solution was washed with sodium hydrogen carbonate, brine
  2. concentrationconcentrated
  3. customto give a white solid

Sources & evidence

ORD record
ord-3613d833b04c46edb17b875e3de05c62
Source dataset
uspto-grants-2005_11
Patent number
US06967216B2

Reaction notes

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