Acetone → 1-(Pyridin-2-yl)butane-1,3-dione

HRID 1726852Notes

Reaction equation

HRID 1726852 reaction equation
[CH3:1][C:2]([CH3:4])=[O:3].[O-]CC.[Na+].[N:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:15](OCC)=[O:16]>O1CCCC1>[N:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:15](=[O:16])[CH2:1][C:2](=[O:3])[CH3:4]

Participants

5

Reactant 3

HCID 180AcetoneHCID 17307Ethyl 2-pyridinecarboxylateHCID 2723922Sodium ethoxide

Product 1

HCID 127072211-(Pyridin-2-yl)butane-1,3-dione

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A solution of 8.71 g (150 mmol) of dry acetone in 100 ml of absolute tetrahydrofuran is added under argon to a solution of 20.42 g (300 mmol) of sodium ethoxide in 300 ml of absolute tetrahydrofuran. A solution of 22.68 g (150 mmol) of ethyl pyridine-2-carboxylate in 100 ml of absolute tetrahydrofuran is subsequently added dropwise over the course of 20 minutes. The mixture is stirred for 15 hours at room temperature and for 4 hours at the boiling point. The mixture is evaporated on a rotary evaporator, admixed with 150 ml of water and rendered neutral with glacial acetic acid. It is extracted twice with diethyl ether, the organic extracts are combined and dried (sodium sulfate), evaporated on a rotary evaporator, and 1-pyridin-2-ylbutane-1,3-dione is obtained as an orange oil. 1H-NMR (360 MHz, CDCl3) for enol tautomer: 15.8-15.5 (br s, OH); 8.60-8.55 (dm, 1H); 8.20-7.95 (dm, 1H); 7.79-7.71 (tm, 1H); 7.35-7.29 (m, 1H); 6.74 (s, 1H); 2.15 (s, 3H). Keto tautomer: CH2 group at 4.20 ppm (ratio of enol/keto form=87:13).

Workup

  1. customThe mixture is evaporated on a rotary evaporator
  2. extractionIt is extracted twice with diethyl ether
  3. dry with materialdried (sodium sulfate)
  4. customevaporated on a rotary evaporator

Sources & evidence

ORD record
ord-f3a5acc29d054d978e448ad8bcadc2be
Source dataset
uspto-grants-2009_02
Patent number
US07494964B2

Reaction notes

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