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

HRID 1171189Notes

Reaction equation

HRID 1171189 reaction equation
[CH2:1]([O:8][C:9]1[CH:19]=[CH:18][C:12]2[CH:13]=[C:14]([CH2:16]O)[O:15][C:11]=2[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:20]1(=[O:30])[NH:24][C:23](=[O:25])[C:22]2=[CH:26][CH:27]=[CH:28][CH:29]=[C:21]12.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>O.O1CCCC1>[CH2:1]([O:8][C:9]1[CH:19]=[CH:18][C:12]2[CH:13]=[C:14]([CH2:16][N:24]3[C:20](=[O:30])[C:21]4[C:22](=[CH:26][CH:27]=[CH:28][CH:29]=4)[C:23]3=[O:25])[O:15][C:11]=2[CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 57608261(6-Benzyloxy-benzofuran-2-yl)-methanol

Product 1

HCID 576082582-(6-Benzyloxy-benzofuran-2-ylmethyl)-isoindole-1,3-dione

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a tetrahydrofuran (300 mL) solution of (6-benzyloxy-benzofuran-2-yl)-methanol (14.2 g, 55.8 mmol) described in Production Example 1-2-2 were added phthalimide (9.03 g, 61.4 mmol), triphenylphosphine (17.6 g, 67 mmol) and diethylazodicarboxylate (29.2 g, 67 mmol) at 0° C., which was stirred at room temperature for 7 hours 30 minutes. To the reaction mixture was added water at room temperature followed by extraction with ethyl acetate. After washing the organic layer with water and sat. NaCl, the organic layer was dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under a reduced pressure and the residue was purified by NH silica gel column chromatography (heptane:ethyl acetate=3:1) to obtain a mixture of the title compound and a by-product (14.3 g) as a white solid. This was then used in the next reaction without additional purification.

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washAfter washing the organic layer with water and sat. NaCl
  3. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated under a reduced pressure
  6. customthe residue was purified by NH silica gel column chromatography (heptane:ethyl acetate=3:1)
  7. customto obtain

Sources & evidence

ORD record
ord-d8bea7a533da49d7a7559af0bb8ffbcf
Source dataset
uspto-grants-2010_11
Patent number
US07829585B2

Reaction notes

Loading…