Methanol → HCID 19421622, compound

HRID 1613314Notes

Reaction equation

HRID 1613314 reaction equation
[C:1]1(/[C:7](/[C:13]#[C:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:8]\[C:9]([O:11]C)=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CO.[OH-].[Na+]>O1CCCC1>[C:1]1(/[C:7](/[C:13]#[C:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:8]\[C:9]([OH:11])=[O:10])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 86746608HCID 86746608, compound

Product 1

HCID 19421622HCID 19421622, compoundYield 96.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 1.000 g of methyl (E)-3,5-diphenylpent-2-en-4-ynoate (prepared as described in Preparation 104), 15 ml of methanol, 7.5 ml of tetrahydrofuran and 15 ml of a 10% w/v aqueous solution of sodium hydroxide was stirred for 18 hours at room temperature. At the end of this time, the solvent was distilled off under reduced pressure. The resulting residue was diluted with water and extracted twice with diethyl ether. The ethereal extracts were washed with water, dried over anhydrous sodium sulfate and condensed by evaporation under reduced pressure, to give 0.912 g of the title compound, melting at 124°-126° C. (after recrystallisation from a mixture of methylene chloride and hexane).

Workup

  1. distillationAt the end of this time, the solvent was distilled off under reduced pressure
  2. additionThe resulting residue was diluted with water
  3. extractionextracted twice with diethyl ether
  4. washThe ethereal extracts were washed with water
  5. dry with materialdried over anhydrous sodium sulfate and condensed by evaporation under reduced pressure

Sources & evidence

ORD record
ord-b2e5849f62454351b99b9688d0102007
Source dataset
uspto-grants-1993_03
Patent number
US05192766

Reaction notes

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