Triacetoxyperiodinane → HCID 131732114, compound

HRID 1398537Notes

Reaction equation

HRID 1398537 reaction equation
[C:1]([SiH2:5][O:6][C:7]([CH3:16])([CH3:15])[C:8]1([CH2:13][OH:14])[CH2:12][CH2:11][CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[C:1]([SiH2:5][O:6][C:7]([CH3:16])([CH3:15])[C:8]1([CH:13]=[O:14])[CH2:9][CH2:10][CH2:11][CH2:12]1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 131732115HCID 131732115, compound

Product 1

HCID 131732114HCID 131732114, compoundYield 68.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

[1-(tert-butyl-dimethyl-silanyloxymethyl)-cyclopentyl]-methanol (1.1 g, 4.51 mmol) was dissolved in DCM (30 ml) and Dess-Martin reagent (3.82 g, 9.0 mmol) was added in portions. The reaction mixture was stirred at room temperature for 4 hr and filtered. The filtrate was concentrated in vacuo and purified by silica gel chromatography (eluted with hexanes:EtOAc, 10:1) to afford the title compound (0.75 g, 64%): 1H NMR (400 MHz, DMSO) delta 0.00 (s, 6H), 0.84 (s, 9H), 1.28-1.31 (m, 4H), 1.46-1.50 (m, 4H), 3.76 (s, 2H), 9.54 (s, 1H).

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated in vacuo
  3. custompurified by silica gel chromatography (eluted with hexanes:EtOAc, 10:1)

Sources & evidence

ORD record
ord-edffa5471e764988b950de9d52f92e1a
Source dataset
uspto-grants-2014_12
Patent number
US08901313B2

Reaction notes

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