Triacetoxyperiodinane → HCID 22730192, compound

HRID 2356136Notes

Reaction equation

HRID 2356136 reaction equation
[OH:1][CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][C:13]([C:16]([O:18][CH3:19])=[O:17])=[CH:12][CH:11]=2)=[C:6]([O:20][CH3:21])[CH:5]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>ClCCl>[CH3:21][O:20][C:6]1[CH:5]=[C:4]([CH2:3][CH:2]=[O:1])[CH:9]=[CH:8][C:7]=1[C:10]1[CH:11]=[CH:12][C:13]([C:16]([O:18][CH3:19])=[O:17])=[CH:14][CH:15]=1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 22730343HCID 22730343, compound

Product 1

HCID 22730192HCID 22730192, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of Example 491B (2.47 g, 8.63 mmol) in dichloromethane (25 mL) at room temperature was treated with Dess-Martin periodinane (4.03 g, 9.49 mmol), stirred for 90 minutes, and concentrated. The concentrate was purified by flash column chromatography on silica gel with 1:1 ethyl acetate/hexanes to provide the desired product.

Workup

  1. concentrationconcentrated
  2. customThe concentrate was purified by flash column chromatography on silica gel with 1:1 ethyl acetate/hexanes

Sources & evidence

ORD record
ord-1d101496434b488fb4086dfbe4325326
Source dataset
uspto-grants-2010_07
Patent number
US07754886B2

Reaction notes

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