Benzaldehyde → 1,2-Diphenylpentane-1,4-dione

HRID 1189558Notes

Reaction equation

HRID 1189558 reaction equation
[CH:1](=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C-]#N.[Na+].[C:12]1(/[CH:18]=[CH:19]/[C:20](=[O:22])[CH3:21])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>CN(C=O)C>[C:2]1([C:1](=[O:8])[CH:18]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:19][C:20](=[O:22])[CH3:21])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 240BenzaldehydeHCID 8929Sodium CyanideHCID 637759Benzylideneacetone

Product 1

HCID 131847301,2-Diphenylpentane-1,4-dioneYield 38.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

A solution of benzaldehyde (10.10 ml, 100 mmol) in DMF (50 ml) was added dropwise in the course of ½ hour to a mixture of sodium cyanide (2.450 g, 50 mmol) in DMF (50 ml) at 35° C. Stirring was continued for 1.5 hours at 35° C. A solution of (E)-4-phenylbut-3-en-2-one (10.9 g, 74.6 mmol) in DMF (50 ml) was slowly added dropwise over the course of 1.5 hours at 35° C. Stirring was continued for 3.5 hours at the same temperature. The reaction was quenched with twice its quantity of water and extracted with DCM, combined extracts were washed with water and brine, dried over Na2SO4, filtered and concentrated to give a liquid residue. This was purified by chromatography on silica gel using an automated Biotage system and EtOAc/Hexanes, 0-50%, to give 1,2-diphenylpentane-1,4-dione (7.3 g, 28.9 mmol, 38.8% yield). 1H NMR (400 MHz, CDCl3) δ (ppm) 7.97-7.94 (m, 2H), 7.49-7.49 (m, 1H), 7.39-7.35 (m, 2H), 7.29-7.20 (m, 5H), 5.10 (dd, 1H), 3.61 (dd, 1H), 2.75 (dd, 1H), 2.19 (s, 3H).

Workup

  1. stirringStirring
  2. waitwas continued for 3.5 hours at the same temperature
  3. customThe reaction was quenched with twice its quantity of water
  4. extractionextracted with DCM
  5. washwere washed with water and brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto give a liquid residue
  10. customThis was purified by chromatography on silica gel using an automated Biotage system and EtOAc/Hexanes, 0-50%

Sources & evidence

ORD record
ord-56a090807c334d2bb6aec6754a651475
Source dataset
uspto-grants-2014_03
Patent number
US08674115B2

Reaction notes

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