Triacetoxyperiodinane → HCID 58026147, compound

HRID 2387307Notes

Reaction equation

HRID 2387307 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:20])([CH3:19])[CH2:9][C@@:10]([C:15]([F:18])([F:17])[F:16])([OH:14])[CH2:11][CH2:12][OH:13])=[C:4]([S:21]([CH3:24])(=[O:23])=[O:22])[CH:3]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:20])([CH3:19])[CH2:9][C@:10]([OH:14])([C:15]([F:17])([F:16])[F:18])[CH2:11][CH:12]=[O:13])=[C:4]([S:21]([CH3:24])(=[O:22])=[O:23])[CH:3]=1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 58026142HCID 58026142, compound

Product 1

HCID 58026147HCID 58026147, compoundYield 87.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

(R)-5-(4-Chloro-2-methanesulfonylphenyl)-5-methyl-3-trifluoromethylhexane-1,3-diol (27.6 g, 0.07 mol) was dissolved in methylene chloride (400 mL) with mild heating (50° C.). Dess-Martin periodinane (33.1 g, 0.08 mol) was added and the mixture was stirred at room temperature. After 1 hour the reaction was concentrated in vacuo, diluted with 300 mL of diethyl ether and filtered through a plug of CELITE® filter aid. The organic layer was washed with six 100 mL portions of saturated aqueous sodium bicarbonate solution followed by brine and drying over magnesium sulfate. The solution was filtered through CELITE® filter aid and the solvent was evaporated to give a viscous oil. The oil was dissolved in 30% Et2O/hexanes and passed through a plug of silica. Evaporation of the eluent provided (R)-5-(4-chloro-2-methanesulfonylphenyl)-3-hydroxy-5-methyl-3-trifluoromethylhexanal as a viscous oil (23.8 g, 87%).

Workup

  1. concentrationAfter 1 hour the reaction was concentrated in vacuo
  2. additiondiluted with 300 mL of diethyl ether
  3. filtrationfiltered through a plug of CELITE®
  4. filtrationfilter aid
  5. washThe organic layer was washed with six 100 mL portions of saturated aqueous sodium bicarbonate solution
  6. dry with materialdrying over magnesium sulfate
  7. filtrationThe solution was filtered through CELITE®
  8. filtrationfilter aid
  9. customthe solvent was evaporated
  10. customto give a viscous oil
  11. customEvaporation of the eluent

Sources & evidence

ORD record
ord-00cc9742ab154a83a1941e4f17fdb359
Source dataset
uspto-grants-2012_09
Patent number
US08268859B2

Reaction notes

Loading…