5-Benzyloxy-2-(4-benzyloxyphenyl)isoindoline → 5-Hydroxy-2-(4-hydroxyphenyl)isoindoline

HRID 853800Notes

Reaction equation

HRID 853800 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[CH2:14][N:13]([C:18]1[CH:23]=[CH:22][C:21]([O:24]CC3C=CC=CC=3)=[CH:20][CH:19]=1)[CH2:12]2)C1C=CC=CC=1>C(O)(C(F)(F)F)=O>[OH:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[CH2:14][N:13]([C:18]1[CH:23]=[CH:22][C:21]([OH:24])=[CH:20][CH:19]=1)[CH2:12]2

Participants

3

Reactant 1

HCID 694728565-Benzyloxy-2-(4-benzyloxyphenyl)isoindoline

Product 1

HCID 694729205-Hydroxy-2-(4-hydroxyphenyl)isoindolineYield 42.6%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

5-Benzyloxy-2-(4-benzyloxyphenyl)isoindoline (400 mg) in TFA (12 mL) was refluxed under nitrogen atmosphere for 1 h and cooled. The solvents were removed under vacuum. The residue was dissolved in ethyl acetate (100 mL) and washed with saturated sodium bicarbonate (twice) then brine. Purification by chromatography on silica gel (eluant: dichloromethane—methanol 95:5) gave the title compound (95 mg) as a tan solid. 1H NMR (DMSO-d6): 9.35 (s, 1H), 8.53 (s, 1H), 7.14 (d, 1H, J=8.4 Hz), 6.75 (s br, 1H), 6.69 (m, 3H), 6.49 (d, 2H, J=8.7 Hz), 4.38 (m, 4H); MS: 228 (MH+).

Workup

  1. temperaturecooled
  2. customThe solvents were removed under vacuum
  3. dissolutionThe residue was dissolved in ethyl acetate (100 mL)
  4. washwashed with saturated sodium bicarbonate (twice) then brine
  5. customPurification by chromatography on silica gel (eluant: dichloromethane—methanol 95:5)

Sources & evidence

ORD record
ord-7290c3167f08488eb813835ec1c34f46
Source dataset
uspto-grants-2007_08
Patent number
US07256201B2

Reaction notes

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