Ethyl Acetate → 1-Benzyl-3-[4-(4-ethoxyphenyl)-4-methylpent-1-en-1-yl]benzene

HRID 543277Notes

Reaction equation

HRID 543277 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl-].[Al+3].[Cl-].[Cl-].[C:11]([C:19]1[CH:20]=[C:21]([CH:25]=[CH:26][CH2:27][C:28]([C:31]2[CH:36]=[CH:35][C:34]([O:37][CH2:38][CH3:39])=[CH:33][CH:32]=2)([CH3:30])[CH3:29])[CH:22]=[CH:23][CH:24]=1)(=O)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(OCC)(=O)C>CCOCC>[CH2:11]([C:19]1[CH:20]=[C:21]([CH:25]=[CH:26][CH2:27][C:28]([C:31]2[CH:36]=[CH:35][C:34]([O:37][CH2:38][CH3:39])=[CH:33][CH:32]=2)([CH3:30])[CH3:29])[CH:22]=[CH:23][CH:24]=1)[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 6451240Aluminum(III) ChlorideHCID 21226445Aluminium lithium hydrideHCID 53914085{3-[4-(4-Ethoxyphenyl)-4-methylpent-1-en-1-yl]phenyl}(phenyl)methanone

Product 1

HCID 544511461-Benzyl-3-[4-(4-ethoxyphenyl)-4-methylpent-1-en-1-yl]benzeneYield 86.5%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Procedure

To 5 ml of dry ether was added 0.1 g of lithium aluminum hydride, and thereinto was added a solution of 0.7 g of aluminum chloride in 10 ml of dry ether. A solution of 0.54 g of 1-(3-benzoylphenyl)-4-(4-ethoxyphenyl)-4-methyl-1-pentene (prepared according to (1) of Synthesis Example 12) in 2 ml of dry ether was added dropwise into the mixture, and refluxed for 30 minutes. After cooling to room temperature, ethyl acetate was added dropwise into the mixture. And the mixture was poured into ice water, and extracted with benzene. The benzene extract was washed with water and dried, and evaporated under reduced pressure, and purified by column chromatography on silica gel (1:2 mixed solvent of benzene and hexane) to give 0.45 g of the desired product.

Workup

  1. temperaturerefluxed for 30 minutes
  2. extractionextracted with benzene
  3. extractionThe benzene extract
  4. washwas washed with water
  5. customdried
  6. customevaporated under reduced pressure
  7. custompurified by column chromatography on silica gel (1:2 mixed solvent of benzene and hexane)

Sources & evidence

ORD record
ord-2b8a0f7d2f284eab92d3a5e4c0c41470
Source dataset
uspto-grants-1987_04
Patent number
US04661501

Reaction notes

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