Hydrochloric Acid → HCID 9926427, compound

HRID 1384888Notes

Reaction equation

HRID 1384888 reaction equation
[O:1]=[C:2]([CH2:8][C:9](=[O:23])[C:10]1[S:11][C:12]([CH2:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:13][CH:14]=1)[C:3]([O:5]CC)=[O:4].[OH-].[Na+].C1COCC1.Cl>CO>[O:1]=[C:2]([CH2:8][C:9](=[O:23])[C:10]1[S:11][C:12]([CH2:15][CH2:16][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)=[CH:13][CH:14]=1)[C:3]([OH:5])=[O:4]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 21183833HCID 21183833, compound

Product 1

HCID 9926427HCID 9926427, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of ethyl 2,4-dioxo-4-(5-phenethylthiophen-2-yl)butanoate (125 mg, 0.378 mmol), aqueous sodium hydroxide (1.2 mL, 1M, 1.2 mmol), and THF (5 mL) in methanol (5 mL) was stirred at rt overnight. The resultant mixture was treated with aq HCl (1.3 mL. 1M), and concentrated under vacuum. The residue was partitioned between brine and dichloromethane. The organic extract was dried over anhydrous magnesium sulfate, filtered, and concentrated under vacuum to provide off-white solid. Recrystallization of the solid from a mixture dichloromethane and hexane provided the title compound. 1H NMR (CDCl3) δ 7.72 (d, J=3.1 Hz, 1H), 7.35-7.15 (m, 5H), 6.94 (s, 1H), 6.86 (d, J=3.1 Hz, 1H), 3.22 (d, J=8.1 Hz, 2H), 3.03 (d, J=8.1 Hz, 2H).

Workup

  1. concentrationconcentrated under vacuum
  2. customThe residue was partitioned between brine and dichloromethane
  3. extractionThe organic extract
  4. dry with materialwas dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. customto provide off-white solid
  8. customRecrystallization of the solid from a mixture dichloromethane and hexane

Sources & evidence

ORD record
ord-a82962135cc443eda53e5fa1b16d039c
Source dataset
uspto-grants-2001_07
Patent number
US06262055B1

Reaction notes

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