Phthalimide → HCID 19611658, compound

HRID 1602387Notes

Reaction equation

HRID 1602387 reaction equation
CCOC(/N=N/C(OCC)=O)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:32]1(=[O:42])[NH:36][C:35](=[O:37])[C:34]2=[CH:38][CH:39]=[CH:40][CH:41]=[C:33]12.[Cl:43][C:44]1[C:52]2[O:51][CH:50]=[CH:49][C:48]=2[C:47]([CH2:53][CH2:54][CH2:55]O)=[CH:46][CH:45]=1>C1COCC1>[Cl:43][C:44]1[C:52]2[O:51][CH:50]=[CH:49][C:48]=2[C:47]([CH2:53][CH2:54][CH2:55][N:36]2[C:32](=[O:42])[C:33]3[C:34](=[CH:38][CH:39]=[CH:40][CH:41]=3)[C:35]2=[O:37])=[CH:46][CH:45]=1

Participants

6

Reactant 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 19611663HCID 19611663, compound

Product 1

HCID 19611658HCID 19611658, compoundYield 88.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Diethylazodicarboxylate (0.35 ml) was added dropwise to a solution of triphenylphosphine (587 mg) and phthalimide (329 mg) in dry THF (10 ml) at 0° under nitrogen. A solution of 3-(7-chloro-benzofuran-4-yl)-propan-1-ol (364 mg) in THF (5 ml) was then added and the mixture allowed to warm to room temperature and stirred for 2 h. The solvent was evaporated and the residue purified by column chromatography, eluting with cyclohexane/ether 3:1 gave the title compound as a colourless solid (521 mg)

Workup

  1. customThe solvent was evaporated
  2. customthe residue purified by column chromatography
  3. washeluting with cyclohexane/ether 3:1

Sources & evidence

ORD record
ord-d19eafdab19f4a85a7a80ed688e878ad
Source dataset
uspto-grants-1999_11
Patent number
US05981572

Reaction notes

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