Phthalimide → 2-(5-(2-Cyclopropylvinyl)thiophen-2-ylmethyl)isoindol-1,3-dione
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]1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
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
- stirringthe solution was stirred for 1 hour
- extractionwas then extracted with ethyl acetate (50 mL)
- washThe organic layer was washed with water
- dry with materialdried over anhydrous magnesium sulfate
- customthe solvent was evaporated in vacuo
- 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
- Patent number
- US07932272B2
Reaction notes
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