Potassium tert-butoxide → HCID 66707807, compound

HRID 1260143Notes

Reaction equation

HRID 1260143 reaction equation
CC(C)([O-])C.[K+].[Cl:7][C:8]1[CH:13]=[C:12]([CH2:14][CH3:15])[C:11]([CH2:16][C:17]([N:19]([CH3:28])[N:20]=[C:21]([CH3:27])[C:22]([O:24]CC)=O)=[O:18])=[C:10]([CH2:29][CH3:30])[CH:9]=1>O1CCCC1.C1(C)C=CC=CC=1>[Cl:7][C:8]1[CH:9]=[C:10]([CH2:29][CH3:30])[C:11]([C:16]2[C:17](=[O:18])[N:19]([CH3:28])[N:20]=[C:21]([CH3:27])[C:22]=2[OH:24])=[C:12]([CH2:14][CH3:15])[CH:13]=1

Participants

5

Reactant 2

HCID 23665647Potassium tert-butoxideHCID 86644526HCID 86644526, compound

Product 1

HCID 66707807HCID 66707807, compoundYield 14.6%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 0.55 g of potassium tert-butoxide in 20 mL of tetrahydrofuran was stirred at 36 to 38° C. under nitrogen atmosphere. To the solution was added dropwise a solution of 0.79 g of ethyl 2-[2-(4-chloro-2,6-diethylphenylacetyl)-2-methylhydrazono]propanoate (compound VI-2) in 15 mL of toluene over about 20 minutes. The mixture was further stirred at the same temperature for 10 minutes. Then, the reaction mixture was concentrated under reduced pressure. To the residue was added 20 mL of ice water, followed by extraction with tert-butyl methyl ether (20 mL×2). An aqueous layer was acidified by an addition of 0.6 g of 35% hydrochloric acid, followed by extraction with ethyl acetate (20 mL×2). The ethyl acetate extracts were combined, washed with an aqueous saturated sodium chloride solution (20 mL×2), dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was subjected to silica gel chromatography (ethyl acetate:hexane=1:4) to give 0.1 g of a solid. The solid was washed with an ethyl acetate-hexane mixture solvent (1:10) and air dried to give 0.07 g of the title compound as a white powder.

Workup

  1. concentrationThen, the reaction mixture was concentrated under reduced pressure
  2. additionTo the residue was added 20 mL of ice water
  3. extractionfollowed by extraction with tert-butyl methyl ether (20 mL×2)
  4. additionAn aqueous layer was acidified by an addition of 0.6 g of 35% hydrochloric acid
  5. extractionfollowed by extraction with ethyl acetate (20 mL×2)
  6. washwashed with an aqueous saturated sodium chloride solution (20 mL×2)
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-251336b42070443784e1dbdb224f428d
Source dataset
uspto-grants-2013_06
Patent number
US08470738B2

Reaction notes

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