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

HRID 1171210ノート

反応式

HRID 1171210 の反応式
[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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-fe5d7a0bd6964dcda982f26f9b88b17f
出典データセット
uspto-grants-2010_11
特許番号
US07829585B2

反応ノート

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