Triacetoxyperiodinane → 1,3-Dihydro-2-benzofuran-5-carbaldehyde

HRID 2261081Notes

Reaction equation

HRID 2261081 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]1

Participants

5

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 19809558(1,3-Dihydro-2-benzofuran-5-yl)methanol

Product 1

HCID 113894701,3-Dihydro-2-benzofuran-5-carbaldehyde

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

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

  1. extractionextracted 2× with NaOH 1N, 2× with H2O
  2. dry with materialdried over MgSO4
  3. 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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