Triacetoxyperiodinane → HCID 69814972, compound

HRID 584160Notes

Reaction equation

HRID 584160 reaction equation
[Si:1]([O:18][CH2:19][CH2:20][CH2:21][C:22]1[CH:48]=[CH:47][C:25]([O:26][C:27]([CH3:46])([CH3:45])[CH:28]([OH:44])[CH2:29][O:30][C:31]2[CH:36]=[CH:35][C:34]([C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])=[CH:33][CH:32]=2)=[CH:24][CH:23]=1)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C1=CC=CC=2)=O>ClCCl.C(OCC)(=O)C>[Si:1]([O:18][CH2:19][CH2:20][CH2:21][C:22]1[CH:23]=[CH:24][C:25]([O:26][C:27]([CH3:46])([CH3:45])[C:28](=[O:44])[CH2:29][O:30][C:31]2[CH:36]=[CH:35][C:34]([C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])=[CH:33][CH:32]=2)=[CH:47][CH:48]=1)([C:14]([CH3:17])([CH3:15])[CH3:16])([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 131725060HCID 131725060, compound

Product 1

HCID 69814972HCID 69814972, compoundYield 98.9%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
22 °C

Procedure

A solution of (2R and 2S)-3-[4-[3-(tert-butyldiphenysilyloxy)propyl]phenoxy]-1-[4-(tert-butoxycarbonyl)phenoxy]-3-methyl-2-butanol (0.60 g, 0.89 mmol) in dry dichloromethane (30 ml) was treated with 1,1,1-triacetoxy-1,1-dihydro-1,2-benziodoxol-3(1H)-one (Dess-Martin periodinane) (1.50 g, 3.57 mmol) and the resulting mixture was stirred at 22° C. for 3 hours. The reaction mixture was diluted with ethyl acetate, washed with 5% sodium thiosulfate, saturated sodium bicarbonate and brine. After drying (magnesium sulfate), the organic phase was concentrated and chromatographed on silica gel. Elution with a mixture of toluene and ethyl acetate (98:2) gave 0.587 g (98%) of the title material as a clear oil.

Workup

  1. washwashed with 5% sodium thiosulfate, saturated sodium bicarbonate and brine
  2. dry with materialAfter drying (magnesium sulfate)
  3. concentrationthe organic phase was concentrated
  4. customchromatographed on silica gel
  5. washElution
  6. additionwith a mixture of toluene and ethyl acetate (98:2)

Sources & evidence

ORD record
ord-864fb1b228cc41f886d8583ca5e85beb
Source dataset
uspto-grants-2005_08
Patent number
US06924391B2

Reaction notes

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