Triacetoxyperiodinane → HCID 22345533, compound

HRID 584149Notes

Reaction equation

[Si:1]([O:18][CH2:19][CH2:20][CH2:21][C:22]1[CH:46]=[CH:45][C:25]([O:26][CH2:27][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][CH2:27][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:45][CH:46]=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

Conditions

Temperature: 22 °C

Procedure

A solution of 3-[4-[3-(tert-butyldiphenylsilyloxy)propyl]phenoxy]-1-[4-(tert-butoxy carbonyl)phenoxy]-2-propanol (2.08 g, 3.25 mmol) in dichloromethane (120 ml) was treated with 1,1,1-triacetoxy-1,1-dihydro-1,2-benziodoxol-3(1H)-one (Dess-Martin periodinane) (5.46 g, 12.9 mmol) and the resulting mixture was stirred at 22° C. for 18 hours. The reaction mixture was then diluted with ethyl acetate, washed with 10% aqueous 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, 95:5) gave 1.82 g (88%) of the title material as oil.

Workup

washwashed with 10% aqueous 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, 95:5)

Sources & evidence

ORD record: ord-48341a84b0154d0e9b419119fdb17ae7
Source dataset: uspto-grants-2005_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06924391B2

Reaction notes

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