Phthalimide → HCID 57608238, compound

HRID 1171204Notes

Reaction equation

HRID 1171204 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]2[O:16][C:15]([CH2:17]O)=[CH:14][C:13]=2[CH:19]=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:10]=[CH:11][C:12]2[O:16][C:15]([CH2:17][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])=[CH:14][C:13]=2[CH:19]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 57608228HCID 57608228, compound

Product 1

HCID 57608238HCID 57608238, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a tetrahydrofuran (10 mL) solution of (5-benzyloxy-benzofuran-2-yl)-methanol (561 mg, 2.21 mmol) described in Production Example 7-1-4 were added phthalimide (358 mg, 2.43 mmol), triphenylphosphine (696 mg, 2.65 mmol) and diethylazodicarboxylate (1.21 mL, 2.65 mmol) at 0° C., which was stirred at room temperature for 9 hours. Water was added to the reaction solution at room temperature 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 (heptane:ethyl acetate=7:3) to obtain the title compound (635 mg, 75%) as a white solid.

Workup

  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 (heptane:ethyl acetate=7:3)

Sources & evidence

ORD record
ord-3eb65cdde2a14b519cb62b481727a576
Source dataset
uspto-grants-2010_11
Patent number
US07829585B2

Reaction notes

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