Triacetoxyperiodinane → HCID 21963908, compound

HRID 2212382Notes

Reaction equation

HRID 2212382 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([C:11]2([C:27]3[CH:32]=[C:31]([F:33])[CH:30]=[CH:29][C:28]=3[F:34])[CH2:16][CH2:15][CH:14]([CH2:17][C:18]([C:20]3[O:21][C:22]([CH2:25][OH:26])=[CH:23][CH:24]=3)=[O:19])[CH2:13][CH2:12]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>ClCCl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([C:11]2([C:27]3[CH:32]=[C:31]([F:33])[CH:30]=[CH:29][C:28]=3[F:34])[CH2:12][CH2:13][CH:14]([CH2:17][C:18]([C:20]3[O:21][C:22]([CH:25]=[O:26])=[CH:23][CH:24]=3)=[O:19])[CH2:15][CH2:16]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 21963916HCID 21963916, compound

Product 1

HCID 21963908HCID 21963908, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of the product from Example 138 (179 mg, 0.35 mmol) in dichloromethane (17 mL) was added Dess-Martin periodinane (374 mg, 0.88 mmol). The reaction was stirred at room temperature for one hour, filtered through Celite®, evaporated, and the residue purified by column chromatography on silica to afford the desired product (94 mg) as a white solid. MS (ES+) 507 ([MH]+).

Workup

  1. filtrationfiltered through Celite®
  2. customevaporated
  3. customthe residue purified by column chromatography on silica

Sources & evidence

ORD record
ord-77885d14c04947e198266f70c5da0b18
Source dataset
uspto-grants-2006_09
Patent number
US07101895B2

Reaction notes

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