Triacetoxyperiodinane → HCID 89601144, compound

HRID 530245Notes

Reaction equation

HRID 530245 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][C:7]([CH:11]([C:13]3[C:18]([CH3:20])([CH3:19])[CH2:17][CH2:16][C:15]([CH3:22])([CH3:21])[CH:14]=3)[OH:12])=[CH:8][CH:9]=2)[CH:4]=[CH:3][N:2]=1.C(=O)(O)[O-].[Na+].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>ClCCl>[CH:1]1[C:10]2[C:5](=[CH:6][C:7]([C:11]([C:13]3[C:18]([CH3:20])([CH3:19])[CH2:17][CH2:16][C:15]([CH3:22])([CH3:21])[CH:14]=3)=[O:12])=[CH:8][CH:9]=2)[CH:4]=[CH:3][N:2]=1

Participants

5

Reactant 3

HCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 89601576HCID 89601576, compound

Product 1

HCID 89601144HCID 89601144, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To the product of Example 10h (167.3 mg, 0.57 mmol) in dichloromethane (10 mL) at room temperature was added sodium bicarbonate (50 mg) and Dess-Martin periodinane (365 mg, 0.85 mmol) and the reaction was stirred at room temperature overnight. The mixture was concentrated under reduced pressure and the residue was purified by silica gel column chromatography to afford the title compound as a colorless oil (130 mg, Yield: 78%). 1H NMR (400 MHz, CDCl3) δ 9.32 (s, 1H), 8.61 (d, J=6.0 Hz, 1H), 8.09 (s, 1H), 8.02 (d, J=8.4 Hz, 1H), 7.91 (d, J=8.4 Hz, 1H), 7.73 (d, J=6.0 Hz, 1H), 5.91 (s, 1H), 1.66-1.59 (m, 4H), 1.31 (s, 6H), 1.07 (s, 6H) ppm.

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-b4e0eb2d5e0746e5ba6878dd6ab52656
Source dataset
uspto-grants-2016_05
Patent number
US09353063B2

Reaction notes

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