Triacetoxyperiodinane → HCID 49820157, compound

HRID 1914783Notes

Reaction equation

HRID 1914783 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][CH:15]=[CH:14][CH:13]=3)=[O:11])[C:6]=2[CH:18]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=[O:21].C(Cl)(Cl)Cl.CO>CS(C)=O>[C:10]([C:7]1[C:6]2[C:18](=[O:21])[C:2](=[O:1])[CH:3]=[CH:4][C:5]=2[O:9][CH:8]=1)(=[O:11])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 159087TriacetoxyperiodinaneHCID 595415(5-Hydroxy-1-benzofuran-3-yl)(phenyl)methanoneHCID 21584188Chloroform methanol

Product 1

HCID 49820157HCID 49820157, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of compound 3 (100 mg, 0.42 mmol) in DMSO (1 mL) was added Dess-Martin periodinane (356 mg, 0.84 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 furnish compound SKC-BF-01 (50 mg, 50%) as a red solid. TLC Rf=0.6 (CHCl3-MeOH, 9:1). NMR (CDCl3) δ 7.88-7.85 (m, 3H), 7.61 (d, J=6.33 Hz, 1H), 7.49 (d, J=7.6 Hz, 2H), 7.41 (d, J=10.3 Hz, 1H), 6.34 (d, J=10.3 Hz, 1H); MS (ES) m/z 253 (M+H)+.

Workup

  1. filtrationThe resulting precipitate was filtered
  2. washwashed with water
  3. customdried under high vacuum
  4. customto furnish compound SKC-BF-01 (50 mg, 50%) as a red solid

Sources & evidence

ORD record
ord-17a1fddb5bf84956bfa5aa7e747cd624
Source dataset
uspto-grants-2013_12
Patent number
US08614237B2

Reaction notes

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