Triacetoxyperiodinane → 1,3-Dihydro-2-benzofuran-5-carbaldehyde
Reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][C:6]([CH2:10][OH:11])=[CH:7][CH:8]=2)[CH2:3][O:2]1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C1=CC=CC=2)=O>C(Cl)Cl.CCOCC>[CH2:1]1[C:9]2[C:4](=[CH:5][C:6]([CH:10]=[O:11])=[CH:7][CH:8]=2)[CH2:3][O:2]1Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
(1,3-Dihydro-isobenzofuran-5-yl)-methanol (440 mg, 2.9 mmol) was dissolved in 20 ml of DCM. 1,1,1-Triacetoxy-1,1-dihydro-1,2-benziodoxol-3(1H)-one (Dess-Martin reagent) (1.3 g, 3.2 mmol) was added and the reaction was stirred at r.t. for 4 h. The reaction mixture was diluted with ether and extracted 2× with NaOH 1N, 2× with H2O and dried over MgSO4. The crude product was sufficiently pure and used without any further purification.
Workup
- extractionextracted 2× with NaOH 1N, 2× with H2O
- dry with materialdried over MgSO4
- customused without any further purification
Sources & evidence
- ORD record
- ord-31980dbb195d4ad78d3ff42198cc8d3a
- Source dataset
- uspto-grants-2010_12
- Patent number
- US07846925B2
Reaction notes
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