Benzaldehyde → 5337-53-1

HRID 1815125Notes

Reaction equation

HRID 1815125 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][N:5]=1)(=[O:3])[CH3:2].[CH:10](=O)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C[O-].[Na+].Cl>CO.O1CCCC1>[CH:14]1[CH:15]=[CH:16][C:11](/[CH:10]=[CH:2]/[C:1]([C:4]2[N:5]=[CH:6][CH:7]=[CH:8][CH:9]=2)=[O:3])=[CH:12][CH:13]=1

Participants

7

Reactant 4

HCID 240BenzaldehydeHCID 313Hydrochloric AcidHCID 142862-AcetylpyridineHCID 10942334Sodium Methoxide

Product 1

HCID 53541195337-53-1

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To solution of 2-acetylpyridine 1a (10 mmol, 1 equiv.) and tetrahydrofuran (25 mL) is added benzaldehyde 1b (10 mmol, 1 equiv.). Sodium methoxide (12 mmol, 1.2 equiv.) in methanol (24 mL, 0.5M) is introduced into the reaction and is agitated for 15 hours at room temperature. Hydrochloric acid (1N) is added until a neutral pH is obtained. The solution is extracted with dichloromethane twice, and washed once with water. The combined organic layers are dried over MgSO4, and concentrated under reduced pressure. The residue is purified by flash column chromatography on SiO2 (33% ethyl acetate/hexanes) to give the 3-phenyl-1-pyridin-2-yl-propenone 1c as a pale yellow solid. See Hollinshead, S. P., Tetrahedron Letters, Vol 37, pp. 9157-9160 (1996).

Workup

  1. customis obtained
  2. extractionThe solution is extracted with dichloromethane twice
  3. washwashed once with water
  4. dry with materialThe combined organic layers are dried over MgSO4
  5. concentrationconcentrated under reduced pressure
  6. customThe residue is purified by flash column chromatography on SiO2 (33% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-072ebe0204224c3196bbc452076bdc69
Source dataset
uspto-grants-2005_04
Patent number
US06878729B2

Reaction notes

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