Triacetoxyperiodinane → HCID 178455323, compound

HRID 516881Notes

Reaction equation

HRID 516881 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[Si:23]([O:30][C@@H:31]1[CH2:36][CH2:35][C@H:34]([CH:37]([OH:48])[C:38]([O:40][CH2:41][C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)=[O:39])[CH2:33][CH2:32]1)([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:25])[CH3:24]>ClCCl>[Si:23]([O:30][C@@H:31]1[CH2:32][CH2:33][C@H:34]([C:37](=[O:48])[C:38]([O:40][CH2:41][C:42]2[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=2)=[O:39])[CH2:35][CH2:36]1)([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:25])[CH3:24]

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 178455324HCID 178455324, compound

Product 1

HCID 178455323HCID 178455323, compoundYield 69.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A Dess-Martin reagent (1.2 g, 2.76 mmol) was added to a solution of benzyl 2-(cis-4-((tert-butyldimethylsilyl)oxy)cyclohexyl)-2-hydroxyacetate (650 mg, 1.72 mmol) in dichloromethane (10 ml) at room temperature, and the mixture was stirred at room temperature for 15 hr. The reaction mixture was quenched with 10% sodium thiosulfate and was extracted with dichloromethane. The organic layer was washed with a saturated aqueous sodium bicarbonate solution, was washed with saturated brine, and was dried over anhydrous magnesium sulfate, and the filtrate was concentrated under reduced pressure. The residue was chromatographed on silica gel column (hexane:ethyl acetate=95:5) to give the title compound as a yellow oil (450 mg, yield 69%).

Workup

  1. customThe reaction mixture was quenched with 10% sodium thiosulfate
  2. extractionwas extracted with dichloromethane
  3. washThe organic layer was washed with a saturated aqueous sodium bicarbonate solution
  4. washwas washed with saturated brine
  5. dry with materialwas dried over anhydrous magnesium sulfate
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customThe residue was chromatographed on silica gel column (hexane:ethyl acetate=95:5)

Sources & evidence

ORD record
ord-3e4c8678aa5443a280c640819d3fc050
Source dataset
uspto-grants-2015_08
Patent number
US09115079B2

Reaction notes

Loading…