Ethanol → HCID 54028767, compound

HRID 637381Notes

Reaction equation

HRID 637381 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].C(O)C.[CH2:10]([C:12](=[C:18]([C:25]1[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:13](OCC)=[O:14])[CH3:11]>CCOCC>[CH2:10]([C:12](=[C:18]([C:25]1[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH2:13][OH:14])[CH3:11]

Participants

5

Reactant 3

HCID 702EthanolHCID 21226445Aluminium lithium hydrideHCID 53921704HCID 53921704, compound

Product 1

HCID 54028767HCID 54028767, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Procedure

1.04 g (30 mmol) of LiAlH4 were suspended in 25 ml of dry ether. 1.38 g (30 mmol) of dry ethanol in ether were cautiously added to this suspension. 16 ml of this reagent were in 2 ml portions at 1 hour intervals added to a stirred solution of 1.86 g (6 mmol) of ethyl 2-ethyl-3-(p-methoxyphenyl)-3-phenylpropenoate in 16 ml of dry ether. After the reaction was complete, ice water was added cautiously and the precipitated aluminium salts were filtered off. The water layer was extracted with ether. The combined ether solutions were dried and evaporated to give 1.24 g (4.6 mmol, 77%) of the oily product as a mixture of E- and Z-isomers.

Workup

  1. filtrationthe precipitated aluminium salts were filtered off
  2. extractionThe water layer was extracted with ether
  3. dry with materialThe combined ether solutions were dried
  4. customevaporated

Sources & evidence

ORD record
ord-01890bdce33e49b98947414221245b1b
Source dataset
uspto-grants-1985_12
Patent number
US04556677

Reaction notes

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