Triacetoxyperiodinane → HCID 49820162, compound

HRID 1914785Notes

Reaction equation

HRID 1914785 reaction equation
Br[C:2]1[C:7]2[C:8]([C:11]([C:13]3[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=3)=[O:12])=[CH:9][O:10][C:6]=2[C:5]([Br:21])=[CH:4][C:3]=1[OH:22].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=[O:25]>CS(C)=O>[Br:21][C:5]1[C:6]2[O:10][CH:9]=[C:8]([C:11](=[O:12])[C:13]3[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=3)[C:7]=2[C:2](=[O:25])[C:3](=[O:22])[CH:4]=1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 56676936HCID 56676936, compound

Product 1

HCID 49820162HCID 49820162, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of compound 7d (50 mg, 0.12 mmol) in DMSO (1.5 mL) was added Dess-Martin periodinane (100 mg, 0.24 mmol) at 0° C. The resulting mixture was stirred at room temperature for 20 min and poured into ice water (2 mL). The resulting precipitate was filtered, washed with water, and dried under high vacuum to obtain compound SKC-BF-07 (25 mg, 55%) as a red solid. TLC Rf=0.45 (petroleum ether-EtOAc, 6:4); 1H NMR (CDCl3) δ 7.89 (s, 1H), 7.85 (d, J=8.7 Hz, 2H), 6.95 (d, J=9.0 Hz, 2H), 6.78 (s, 1H), 3.89 (s, 3H); MS (ES) m/z 362 (M+H)+.

Workup

  1. filtrationThe resulting precipitate was filtered
  2. washwashed with water
  3. customdried under high vacuum
  4. customto obtain compound SKC-BF-07 (25 mg, 55%) as a red solid

Sources & evidence

ORD record
ord-28158868e1fd49abb7090fa88459d453
Source dataset
uspto-grants-2013_12
Patent number
US08614237B2

Reaction notes

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