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

HRID 853800ノート

反応式

HRID 853800 の反応式
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

参加物

3

反応物 1

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

生成物 1

HCID 694729205-Hydroxy-2-(4-hydroxyphenyl)isoindoline収率 42.6%

試薬・触媒・溶媒 1

HCID 6422Trifluoroacetic acid溶媒

実験手順

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+).

後処理

  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)

出典と根拠

ORDレコード
ord-7290c3167f08488eb813835ec1c34f46
出典データセット
uspto-grants-2007_08
特許番号
US07256201B2

反応ノート

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