Phthalimide → 2-(6-Phenoxy-benzofuran-2-ylmethyl)-isoindole-1,3-dione

HRID 1171210노트

반응식

HRID 1171210 반응식
[O:1]([C:8]1[CH:18]=[CH:17][C:11]2[CH:12]=[C:13]([CH2:15]O)[O:14][C:10]=2[CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:19]1(=[O:29])[NH:23][C:22](=[O:24])[C:21]2=[CH:25][CH:26]=[CH:27][CH:28]=[C:20]12.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>O.O1CCCC1>[O:1]([C:8]1[CH:18]=[CH:17][C:11]2[CH:12]=[C:13]([CH2:15][N:23]3[C:19](=[O:29])[C:20]4[C:21](=[CH:25][CH:26]=[CH:27][CH:28]=4)[C:22]3=[O:24])[O:14][C:10]=2[CH:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

7

반응물 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 57608210(6-Phenoxy-benzofuran-2-yl)-methanol

생성물 1

HCID 576082842-(6-Phenoxy-benzofuran-2-ylmethyl)-isoindole-1,3-dione수율 77%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

To a tetrahydrofuran (4 mL) solution of (6-phenoxy-benzofuran-2-yl)-methanol (177 mg, 737 μmol) described in Production Example 49-1-2 were added phthalimide (119 mg, 811 μmol), triphenylphosphine (232 mg, 884 μmol) and diethylazodicarboxylate (403 μL, 884 mmol) at 0° C., which was stirred at room temperature for 4 hours and 30 minutes. Water was added to the reaction solution followed by extraction with ethyl acetate. The organic layer was washed with sat. NaCl followed by drying over anhydrous magnesium sulfate and filtering. The filtrate was concentrated under a reduced pressure and the residue was purified by NH silica gel column chromatography (hexane:ethyl acetate=5:1) to obtain the title compound (209 mg, 77%) as a colorless oil.

후처리

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed with sat. NaCl
  3. dry with materialby drying over anhydrous magnesium sulfate
  4. filtrationfiltering
  5. concentrationThe filtrate was concentrated under a reduced pressure
  6. customthe residue was purified by NH silica gel column chromatography (hexane:ethyl acetate=5:1)

출처 및 근거

ORD 기록
ord-fe5d7a0bd6964dcda982f26f9b88b17f
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07829585B2

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