Potassium Hydroxide → HCID 69338235, compound

HRID 2086178Notes

Reaction equation

HRID 2086178 reaction equation
[CH2:1]([O:3][C:4](=[O:19])[C:5]([CH2:12][CH2:13][C:14]1[S:15][CH:16]=[CH:17][CH:18]=1)([CH3:11])[C:6]([O:8]CC)=[O:7])[CH3:2].[OH-].[K+]>C(O)C.O>[CH2:1]([O:3][C:4](=[O:19])[C:5]([CH2:12][CH2:13][C:14]1[S:15][CH:16]=[CH:17][CH:18]=1)([CH3:11])[C:6]([OH:8])=[O:7])[CH3:2]

Participants

5

Reactant 2

HCID 14797Potassium Hydroxide2×HCID 85759744Propanedioic acid, methyl[2-(2-thienyl)ethyl]-, diethyl ester

Product 1

HCID 69338235HCID 69338235, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

2-Methyl-2-(2-thienyl)ethylmalonic acid diethylester (52.7 g, 0.19 mol) obtained in Example 1(a) was dissolved in a mixture of ethanol (240 ml) and water (80 ml), potassium hydroxide (11.4 g, 0.20 mol) was added thereto in an ice bath, and the solution was stirred for 2 hours. And then potassium hydroxide (5.7 g, 0.1 mol) was added thereto three times, one portion every 1 hour, and the reaction solution was stirred for 6 hours in total. Water (300 ml) and ice-cold 10% hydrochloric acid (500 ml) were added to the reaction solution, and the solution was extracted with ethyl acetate. The organic layer was washed with a saturated aqueous sodium chloride solution, and dried over anhydrous magnesium sulfate. The solvent was concentrated in vacuo, and the residue was purified by flash chromatography on a silica gel column (elution solvent; hexane:ethyl acetate=2:1-0:1) to afford the title compound (28.6 g, 60% yield) as a pale yellow oil.

Workup

  1. additionwas added
  2. stirringthree times, one portion every 1 hour, and the reaction solution was stirred for 6 hours in total
  3. extractionthe solution was extracted with ethyl acetate
  4. washThe organic layer was washed with a saturated aqueous sodium chloride solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationThe solvent was concentrated in vacuo
  7. customthe residue was purified by flash chromatography on a silica gel column (elution solvent; hexane:ethyl acetate=2:1-0:1)

Sources & evidence

ORD record
ord-b30740d53aa54f6593112a65ed93a6fe
Source dataset
uspto-grants-2004_04
Patent number
US06723745B2

Reaction notes

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