Tetrahydrofuran → HCID 19432430, compound

HRID 654636Notes

Reaction equation

HRID 654636 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[C:9]3[CH:10]=[CH:11][C:12]([C:14]([O:16]C)=[O:15])=[CH:13][C:8]=3[O:7][C:6]=2[CH:18]=1.C1COCC1.[OH-].[Na+]>CO>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[C:9]3[CH:10]=[CH:11][C:12]([C:14]([OH:16])=[O:15])=[CH:13][C:8]=3[O:7][C:6]=2[CH:18]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 19432434HCID 19432434, compound

Product 1

HCID 19432430HCID 19432430, compoundYield 101.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a mixture of methyl 3-bromo-dibenzofuran-7-carboxylate (3.2 g, 10.5 mmol) in 2:1 THF:methanol (90 ml) was added 2.5N NaOH (60 ml). After stirring at room temperature for 1 hour, the reaction was complete. Nearly all the THF:methanol was evaporated off and then the mixture was adjusted to pH=1 with concentrated HCl and extracted with ethyl acetate. Drying (MgSO4) and evaporation yielded 3.1 g (100%) of the title compounds which was used in the next reaction without purification.

Workup

  1. customNearly all the THF:methanol was evaporated off
  2. extractionextracted with ethyl acetate
  3. customDrying
  4. custom(MgSO4) and evaporation

Sources & evidence

ORD record
ord-a8250362d2164b469a04816975c2000c
Source dataset
uspto-grants-1992_07
Patent number
US05132420

Reaction notes

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