Triacetoxyperiodinane → HCID 49820158, compound

HRID 1914786Notes

Reaction equation

HRID 1914786 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][CH:8]=[C:7]([C:10]([C:12]3[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=3)=[O:11])[C:6]=2[CH:20]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=[O:23].C(Cl)(Cl)Cl.CO>CS(C)=O>[CH3:19][O:18][C:15]1[CH:16]=[CH:17][C:12]([C:10]([C:7]2[C:6]3[C:20](=[O:23])[C:2](=[O:1])[CH:3]=[CH:4][C:5]=3[O:9][CH:8]=2)=[O:11])=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 159087TriacetoxyperiodinaneHCID 687117(5-hydroxy-1-benzofuran-3-yl)(4-methoxyphenyl)methanoneHCID 21584188Chloroform methanol

Product 1

HCID 49820158HCID 49820158, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of compound 9 (100 mg, 0.371 mmol) in DMSO (1.5 mL) was added Dess-Martin periodinane (315 mg, 0.743 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-02 (50 mg, 50%) as a red solid. Rf=0.6 (CHCl3-MeOH, 9:1); 1H NMR (CDCl3) δ 7.85 (d, J=9.0 Hz, 2H), 7.81 (s, 1H), 7.40 (d, J=10.3 Hz, 1H), 6.93 (d, J=9.0 Hz, 2H), 6.32 (d, J=10.3 Hz, 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-02 (50 mg, 50%) as a red solid

Sources & evidence

ORD record
ord-19b99308c98c45dfb531f55ffbeb10ee
Source dataset
uspto-grants-2013_12
Patent number
US08614237B2

Reaction notes

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