Ethanol → HCID 20382854, compound

HRID 1447953Notes

Reaction equation

HRID 1447953 reaction equation
[F:1][C:2]1[C:10]([F:11])=[C:9]([F:12])[C:8]([F:13])=[C:7]2[C:3]=1[CH2:4][N:5]([CH:14]([CH:32]([CH3:34])[CH3:33])[C:15]([O:17]CC1C=CC=C(OC3C=CC=CC=3)C=1)=[O:16])[CH2:6]2.[OH-].[K+].C(O)C>O>[F:13][C:8]1[C:9]([F:12])=[C:10]([F:11])[C:2]([F:1])=[C:3]2[C:7]=1[CH2:6][N:5]([CH:14]([CH:32]([CH3:34])[CH3:33])[C:15]([OH:17])=[O:16])[CH2:4]2

Participants

5

Reactant 3

HCID 702EthanolHCID 14797Potassium HydroxideHCID 20382856HCID 20382856, compound

Product 1

HCID 20382854HCID 20382854, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of m-phenoxybenzyl 2-(4,5,6,7-tetrafluoro-2-isoindolinyl)-3-methylbutanoate (0.4 g), potassium hydroxide (0.134 g), ethanol (8 ml) and water (2 ml) is heated to reflux for 4 hours. After cooling, the reaction mixture is concentrated under vacuum and 50 ml of water is added. This mixture is washed with ether (3×). The aqueous phase is carefully adjusted to pH 7 and then extracted with ether (3×). The combined ether extracts are washed with water, dried and solvent removed under vacuum to yield 2-(4,5,6,7-tetrafluoro-2-isoindolinyl)-3-methylbutanoic acid, a white powder.

Workup

  1. temperatureis heated
  2. temperatureto reflux for 4 hours
  3. temperatureAfter cooling
  4. concentrationthe reaction mixture is concentrated under vacuum and 50 ml of water
  5. additionis added
  6. washThis mixture is washed with ether (3×)
  7. extractionextracted with ether (3×)
  8. washThe combined ether extracts are washed with water
  9. customdried
  10. customsolvent removed under vacuum

Sources & evidence

ORD record
ord-9eeb8b7f7d8b4c99a25caa0928ddd9ef
Source dataset
uspto-grants-1979_12
Patent number
US04178293

Reaction notes

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