Tetrahydrofuran → HCID 58237058, compound

HRID 1188936Notes

Reaction equation

HRID 1188936 reaction equation
[CH3:1][O:2][CH2:3][CH:4]([CH3:31])[O:5][C:6]1[CH:7]=[C:8]([O:20][C:21]2[CH:26]=[CH:25][C:24]([S:27]([CH3:30])(=[O:29])=[O:28])=[CH:23][CH:22]=2)[CH:9]=[C:10]2[C:14]=1[NH:13][C:12]([C:15]([O:17]CC)=[O:16])=[CH:11]2.O1CCCC1.[OH-].[Na+]>C(O)C>[CH3:1][O:2][CH2:3][CH:4]([CH3:31])[O:5][C:6]1[CH:7]=[C:8]([O:20][C:21]2[CH:26]=[CH:25][C:24]([S:27]([CH3:30])(=[O:29])=[O:28])=[CH:23][CH:22]=2)[CH:9]=[C:10]2[C:14]=1[NH:13][C:12]([C:15]([OH:17])=[O:16])=[CH:11]2

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium Hydroxide2×HCID 58237042HCID 58237042, compound

Product 1

HCID 58237058HCID 58237058, compoundYield 58.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

To a mixture of ethyl 7-(2-methoxy-1-methylethoxy)-5-[4-(methylsulfonyl)phenoxy]-1H-indole-2-carboxylate (2.36 g), tetrahydrofuran (20 mL) and ethanol (20 mL) was added 1M aqueous sodium hydroxide solution (7.9 mL). The mixture was stirred at 50° C. for 2 h and at room temperature over night. To the mixture was added 1M aqueous sodium hydroxide solution (10.5 mL). The whole was stirred at 50° C. for further 1 h. The reaction mixture was concentrated in vacuo. The residue was acidified with 1M hydrochloric acid. Ethyl acetate and water were added to the mixture and the organic layer was separated. The organic layer was washed with water, dried (MgSO4), filtered, and concentrated in vacuo. The residue was triturated and washed with hexane to give the title compound (1.288 g, 58%) as a pink solid. The solid was recrystallized from ethyl acetate-hexane to give white crystals. mp 135.9-137.4° C.

Workup

  1. stirringThe whole was stirred at 50° C. for further 1 h
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. additionEthyl acetate and water were added to the mixture
  4. customthe organic layer was separated
  5. washThe organic layer was washed with water
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue was triturated
  10. washwashed with hexane

Sources & evidence

ORD record
ord-1e47f5c9a16949379486cf5294063c5e
Source dataset
uspto-grants-2014_03
Patent number
US08673942B2

Reaction notes

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