3-Phenylprop-2-Enal → HCID 70228646, compound

HRID 1976290Notes

Reaction equation

HRID 1976290 reaction equation
[CH3:1][O:2][C:3](=[O:9])[CH2:4][C:5](=[O:8])[CH2:6][CH3:7].[H-].[Na+].C([Li])CCC.[C:17]1([CH:23]=[CH:24][CH:25]=[O:26])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.Cl>O1CCCC1.CCCCCC.C(OCC)C.O>[CH3:1][O:2][C:3](=[O:9])[CH:4]=[C:5]([OH:8])[CH:6]([CH3:7])[CH:25]([OH:26])[CH:24]=[CH:23][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

10

Reactant 5

HCID 3073-Phenylprop-2-EnalHCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 121699Methyl 3-oxovalerateHCID 178418339Butyllithium

Product 1

HCID 70228646HCID 70228646, compoundYield 114.5%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

13.0 g 3-Oxo-pentanoic acid methyl ester were added to a suspension of 4.4 g of sodium hydride in 250 ml tetrahydrofurane at 0° C. within over a period of about ten minutes and the reaction mixture is stirred for an additional ten minutes. Subsequently, 42.4 ml of butyl lithium in n-hexane (2.5 molar) were added at 0° C. over a period of fifteen minutes and the reaction mixture was stirred for ten minutes. 14.5 g of 3-phenyl-propenal is then added. After stirring, the reaction mixture for ten minutes, 20 ml concentrated hydrochloric acid, 50 ml water and 350 ml diethylether were added successively. The organic phase was separated off, washed and dried. The solvent was removed in vacuo to yield 30 g of an oil having a refraction index of 1.547 at 20° C. The oil was used for the preparation of 7-phenyl-3,5-dimethoxy-4-methyl-hepta-2,6-dienoic acid methyl esters without further purification.

Workup

  1. stirringthe reaction mixture was stirred for ten minutes
  2. stirringAfter stirring
  3. waitthe reaction mixture for ten minutes
  4. customThe organic phase was separated off
  5. washwashed
  6. customdried
  7. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-e1455c91693a4fc79187a2b5e33c0685
Source dataset
uspto-grants-2001_05
Patent number
US06225484B1

Reaction notes

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