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

HRID 853800노트

반응식

HRID 853800 반응식
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

참가 물질

3

반응물 1

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

생성물 1

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

시약·촉매·용매 1

HCID 6422Trifluoroacetic acid용매

실험 절차

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+).

후처리

  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)

출처 및 근거

ORD 기록
ord-7290c3167f08488eb813835ec1c34f46
출처 데이터셋
uspto-grants-2007_08
특허 번호
US07256201B2

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