Diethyl Oxalate → HCID 9926427, compound

HRID 1384887Notes

Reaction equation

HRID 1384887 reaction equation
[C:1]([C:4]1[S:5][C:6]([C:9]#[C:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:7][CH:8]=1)(=[O:3])[CH3:2].[C:17](OCC)(=[O:23])[C:18]([O:20]CC)=[O:19].[O-]CC.[Na+]>C1COCC1.ClCCl>[O:23]=[C:17]([CH2:2][C:1](=[O:3])[C:4]1[S:5][C:6]([CH2:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:7][CH:8]=1)[C:18]([OH:20])=[O:19]

Participants

6

Reactant 3

HCID 7268Diethyl OxalateHCID 2723922Sodium ethoxideHCID 27791981-[5-(Phenylethynyl)thiophen-2-yl]ethan-1-one

Product 1

HCID 9926427HCID 9926427, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2-acetyl-5-(phenylethynyl)thiophene (1.81 g, 8.02 mmol), diethyl oxalate (2.17 mL, 16 mmol), and sodium ethoxide (1.09 g, 16 mmol) in anhydrous THF (25 mL) was stirred at rt under an atmosphere of argon for 5 hr. The resultant mixture was diluted with dichloromethane, and washed successively with dilute HCl, and brine. The organic extract was dried over anhydrous magnesium sulfate, filtered, and concentrated under vacuum to provide yellow solid. Recrystallization of the solid from a mixture dichloromethane and hexane provided the title compound.

Workup

  1. washwashed successively with dilute HCl, and brine
  2. extractionThe organic extract
  3. dry with materialwas dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum
  6. customto provide yellow solid
  7. customRecrystallization of the solid from a mixture dichloromethane and hexane

Sources & evidence

ORD record
ord-28c1e1cc0a154850aac7295c1f2f3990
Source dataset
uspto-grants-2001_07
Patent number
US06262055B1

Reaction notes

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