Triacetoxyperiodinane → HCID 22345545, compound

HRID 584159Notes

Reaction equation

[Si:1]([O:18][CH2:19][CH2:20][CH2:21][C:22]1[CH:33]=[CH:32][C:25]([O:26][C:27]([CH3:31])([CH3:30])[CH2:28][OH:29])=[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:33]=[CH:32][C:25]([O:26][C:27]([CH3:31])([CH3:30])[CH:28]=[O:29])=[CH:24][CH:23]=1)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

Conditions

Temperature: 22 °C

Procedure

A solution of 2-[4-[3-(tert-butyldiphenylsilyloxy)propyl]phenoxy]-2-methyl propanol (5.14 g, 11.1 mmol) in dry dichloromethane (150 ml) was treated with 1,1,1-triacetoxy-1,1-dihydro-1,2-benziodoxol-3(1H)-one (Dess-Martin periodi-nane) (19.2 g, 45.3 mmol) and the resulting mixture was stirred at 22° C. for 3 hours. The reaction mixture was then diluted with ethyl acetate, washed with 5% sodium thiosulfate, saturated sodium bicarbonate, brine and dried (magnesium sulfate). Evaporation of the solvent and chromatography of the residue on silica gel (elution toluene ethyl acetate, 99:1) gave 3.25 g (63%) of the title material as a clear oil.

Workup

washwashed with 5% sodium thiosulfate, saturated sodium bicarbonate, brine
dry with materialdried (magnesium sulfate)
customEvaporation of the solvent and chromatography of the residue on silica gel (elution toluene ethyl acetate, 99:1)

Sources & evidence

ORD record: ord-d97855649ff24f11a119dc944b6cb160
Source dataset: uspto-grants-2005_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06924391B2

Reaction notes

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