Triacetoxyperiodinane → HCID 49820159, compound

HRID 1914788Notes

Reaction equation

HRID 1914788 reaction equation
Cl[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]([Cl: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>[Cl: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 56680248HCID 56680248, compound

Product 1

HCID 49820159HCID 49820159, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of compound 10e (100 mg, 0.29 mmol) in DMSO (1.5 mL) was added Dess-Martin periodinane (253 mg, 0.59 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-03 (50 mg, 53%) as an orange solid. TLC Rf=0.5 (petroleum ether-EtOAc, 6:4); 1H NMR (CDCl3) δ 7.90-7.84 (m, 3H), 6.95 (d, J=8.6 Hz, 2H), 6.53 (s, 1H), 3.88 (s, 3H); MS (ES) m/z 317 (M+H)+.

Workup

  1. filtrationThe resulting precipitate was filtered
  2. washwashed with water
  3. customdried under high vacuum
  4. customto obtain compound SKC-BF-03 (50 mg, 53%) as an orange solid

Sources & evidence

ORD record
ord-e41b9badd5ad4e748f6eb3f6a0a90198
Source dataset
uspto-grants-2013_12
Patent number
US08614237B2

Reaction notes

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