Sodium Hydroxide → HCID 19759911, compound

HRID 1586856Notes

Reaction equation

HRID 1586856 reaction equation
[S:1]1[C:5]2[S:6][CH2:7][CH2:8][C:4]=2[CH:3]=[C:2]1[C:9]([O:11]C)=[O:10].[OH-].[Na+]>C1COCC1.O>[S:1]1[C:5]2[S:6][CH2:7][CH2:8][C:4]=2[CH:3]=[C:2]1[C:9]([OH:11])=[O:10]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 19759902Methyl 4,5-dihydrothieno[2,3-b]thiophene-2-carboxylate

Product 1

HCID 19759911HCID 19759911, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Methyl 4,5-dihydrothieno[2,3-b]thiophene-2-carboxylate (9.5 g, 50 mmol) was dissolved in 200 mL THF followed by treatment with 100 mL of 20% sodium hydroxide and stirred overnight. THF was removed in vacuo to give a dark residue. The residue was taken up in water and extracted with ethyl acetate two times. The aqueous phase was then acidified to pH<1 with conc. HCl and extracted 3×200 mL ethyl acetate. The combined extracts were washed with: 1× water, 2× brine followed by drying over magnesium sulfate. The solution was filtered and the solvent evaporated to give the title compound as a solid (8.1 g). 1H NMR (300 MHz,DMSO-d6) d 2.5(t,2H), 2.8(t,2H), 7.5(s,1H), 12.8(bs,1H exch).

Workup

  1. customTHF was removed in vacuo
  2. customto give a dark residue
  3. extractionextracted with ethyl acetate two times
  4. extractionextracted 3×200 mL ethyl acetate
  5. washThe combined extracts were washed with: 1× water, 2× brine
  6. dry with materialby drying over magnesium sulfate
  7. filtrationThe solution was filtered
  8. customthe solvent evaporated

Sources & evidence

ORD record
ord-2788891232c04f32858dc1e6cedbb4d7
Source dataset
uspto-grants-1993_06
Patent number
US05216020

Reaction notes

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