Benzoylacetone → 1-Phenylhept-6-ene-1,3-dione

HRID 1471856Notes

Reaction equation

HRID 1471856 reaction equation
[C:1]1([C:7](=[O:12])[CH2:8][C:9](=[O:11])[CH3:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[Li+].[CH3:16][CH:17]([N-]C(C)C)[CH3:18].[Li]CCCC.C(NC(C)C)(C)C.BrCC=C>C1COCC1>[C:1]1([C:7](=[O:12])[CH2:8][C:9](=[O:11])[CH2:10][CH2:18][CH:17]=[CH2:16])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

8

Reactant 6

HCID 7166BenzoylacetoneHCID 7841Allyl bromideHCID 7912DiisopropylamineHCID 24758Sodium hydrideHCID 2724682Lithium diisopropylamideHCID 178418339Butyllithium

Product 1

HCID 142891781-Phenylhept-6-ene-1,3-dione

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 1-phenylbutane-1,3-dione (5 g, 30.8 mmol) in THF (50 mL) was added sodium hydride (0.740 g, 30.8 mmol) at 0° C. After warming and stirring at room temperature for 30 min, LDA, which was made by adding BuLi (1.975 g, 30.8 mmol) to a solution of diisopropylamine (4.39 mL, 30.8 mmol) in THF (50 mL) at −45° C., was added at 0° C. After stirring for 30 min at the same temperature, 3-bromoprop-1-ene (3.73 g, 30.8 mmol) was added at 0° C. After stirring for 1 h, the reaction was quenched with 1.0 M HCl and extracted with ethyl acetate. The organic extract was dried over MgSO4 and concentrated under reduced pressure to give the title compound without further purification. LCMS m/z=203.19 [M+H]+.

Workup

  1. temperatureAfter warming
  2. additionwas added at 0° C
  3. additionwas added at 0° C
  4. stirringAfter stirring for 1 h
  5. customthe reaction was quenched with 1.0 M HCl
  6. extractionextracted with ethyl acetate
  7. extractionThe organic extract
  8. dry with materialwas dried over MgSO4
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-2319b11555a54a26a0867c718e435b38
Source dataset
uspto-grants-2015_04
Patent number
US09012478B2

Reaction notes

Loading…