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Phthalimide → 2-(5-(2-Cyclopropylvinyl)thiophen-2-ylmethyl)isoindol-1,3-dione

HRID 2080140
Notes
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Reaction equation

HRID 2080140 reaction equation
[CH:1]1([CH:4]=[CH:5][C:6]2[S:10][C:9]([CH2:11]O)=[CH:8][CH:7]=2)[CH2:3][CH2:2]1.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.COC(N=NC(OC)=O)=O>O1CCCC1.O>[CH:1]1([CH:4]=[CH:5][C:6]2[S:10][C:9]([CH2:11][N:36]3[C:32](=[O:42])[C:33]4[C:34](=[CH:38][CH:39]=[CH:40][CH:41]=4)[C:35]3=[O:37])=[CH:8][CH:7]=2)[CH2:2][CH2:3]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 351621Azodicarboxylic acid dimethyl esterHCID 67119677(5-(2-Cyclopropylvinyl)thiophen-2-yl)methanol

Product 1

HCID 671195832-(5-(2-Cyclopropylvinyl)thiophen-2-ylmethyl)isoindol-1,3-dioneYield 20.6%

Reagents, catalysts & solvents 2

HCID 962
Water
Solvent
HCID 8028TetrahydrofuranSolvent

Procedure

(5-(2-Cyclopropylvinyl)thiophen-2-yl)methanol described in Preparation Example 149 (930 mg, 5.19 mmol), triphenylphosphine (2040 mg, 7.78 mmol) and phthalimide (1140 mg, 7.78 mmol) were dissolved in tetrahydrofuran (50 mL), azodicarboxylic acid dimethyl ester (1140 mg, 7.78 mmol) was added under stirring at room temperature, and the solution was stirred for 1 hour. Water (50 mL) was added to the reaction solution, which was then extracted with ethyl acetate (50 mL). The organic layer was washed with water, dried over anhydrous magnesium sulfate, and the solvent was evaporated in vacuo. The residue was purified by NH silica gel column chromatography (hexane:ethyl acetate=9:1), and the title compound (330 mg, 1.07 mmol, 20.6%) was obtained as a white solid.

Workup

  1. stirringthe solution was stirred for 1 hour
  2. extractionwas then extracted with ethyl acetate (50 mL)
  3. washThe organic layer was washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated in vacuo
  6. customThe residue was purified by NH silica gel column chromatography (hexane:ethyl acetate=9:1)

Sources & evidence

ORD record
ord-2d298c00649e4899b21c8af722e2b048
Source dataset
uspto-grants-2011_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07932272B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes