Triacetoxyperiodinane → 2-(1,3-Dioxaindan-5-yl)acetaldehyde

HRID 747270Notes

Reaction equation

HRID 747270 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][CH2:11][OH:12])=[CH:9][C:4]=2[O:3][CH2:2]1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>ClCCl>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][CH:11]=[O:12])=[CH:9][C:4]=2[O:3][CH2:2]1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 27598462-(1,3-Dioxaindan-5-yl)ethan-1-ol2×

Product 1

HCID 2678892-(1,3-Dioxaindan-5-yl)acetaldehydeYield 76.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2-benzo[1,3]dioxol-5-yl-ethanol (Intermediate D2) (1 g; 6.0 mmol) in dichloromethane (40 mL) was treated with the Dess-Martin periodinane (commercially available from Lancaster) (2.65 g, 6.25 mmol) at rt for 2 h. Silica gel was added to the mixture and the solvent was removed under vacuum. The solids were placed onto a column of silica gel and the product was eluted with a mixture of ether:hexanes to give benzo[1,3]dioxol-5-yl-acetaldehyde (Intermediate D3) 0.75 g.

Workup

  1. additionSilica gel was added to the mixture
  2. customthe solvent was removed under vacuum
  3. washthe product was eluted with a mixture of ether

Sources & evidence

ORD record
ord-a66f5481f8fc4512a9d8b26c2feca872
Source dataset
uspto-grants-2008_07
Patent number
US07396849B2

Reaction notes

Loading…