Triacetoxyperiodinane → HCID 23592303, compound

HRID 1611670Notes

Reaction equation

HRID 1611670 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[Cl:23][C:24]1[CH:29]=[CH:28][C:27]([S:30]([N:33]([C:40]2[CH:45]=[C:44]([Cl:46])[CH:43]=[CH:42][C:41]=2[Cl:47])[C@H:34]([CH3:39])[CH2:35][CH2:36][CH2:37][OH:38])(=[O:32])=[O:31])=[CH:26][CH:25]=1>ClCCl>[Cl:23][C:24]1[CH:25]=[CH:26][C:27]([S:30]([N:33]([C:40]2[CH:45]=[C:44]([Cl:46])[CH:43]=[CH:42][C:41]=2[Cl:47])[C@H:34]([CH3:39])[CH2:35][CH2:36][CH:37]=[O:38])(=[O:32])=[O:31])=[CH:28][CH:29]=1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 23592309HCID 23592309, compound

Product 1

HCID 23592303HCID 23592303, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of Dess-Martin periodinane (4.24 g, 10.0 mmol) in dichloromethane (100 mL) at 0° C. was added dropwise 4-chloro-N-(2,5-dichlorophenyl)-N-(1R)(4-hydroxy-1-methylbutyl)benzenesulfonamide (3.60 g, 8.8 mmol) in dichloromethane (50 mL). The reaction was allowed to slowly come to room temperature with stirring over 18 h. The reaction was then quenched with a saturated solution of 1:1 NaHCO3/NaHSO3 (25 mL) and diluted with EtOAc. The organic phase was washed with H2O and brine, dried over MgSO4, filtered, and concentrated in vacuo. Flash silica gel chromatography (silica gel, 20% EtOAc/hexanes) of the concentrate afforded the title compound as a white wax (1.85 g, 51% yield): 1H NMR (CDCl3) δ 9.70 (s, 1H), 7.68–7.75 (m, 2H), 6.98–7.49 (m, 5H), 4.80–4.85 (m, 1H), 2.36–3.00 (m, 2H), 1.17–1.36 (m, 3H).

Workup

  1. customto slowly come to room temperature
  2. customThe reaction was then quenched with a saturated solution of 1:1 NaHCO3/NaHSO3 (25 mL)
  3. additiondiluted with EtOAc
  4. washThe organic phase was washed with H2O and brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-defb6a9a9f2148d9b6e10c2d97b05683
Source dataset
uspto-grants-2006_01
Patent number
US06989399B2

Reaction notes

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