Triacetoxyperiodinane → HCID 18448167, compound

HRID 1269350Notes

Reaction equation

HRID 1269350 reaction equation
[C:1](=[O:30])([O:8][CH2:9]/[C:10](/[C:20]1[CH:25]=[CH:24][C:23]([S:26]([CH3:29])(=[O:28])=[O:27])=[CH:22][CH:21]=1)=[C:11](/[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)\[CH2:12][OH:13])[O:2][CH2:3][CH2:4][CH2:5][CH2:6][Br:7].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=[O:33]>ClCCl>[Br:7][CH2:6][CH2:5][CH2:4][CH2:3][O:2][C:1]([O:8][CH2:9]/[C:10](/[C:20]1[CH:25]=[CH:24][C:23]([S:26]([CH3:29])(=[O:27])=[O:28])=[CH:22][CH:21]=1)=[C:11](/[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)\[C:12]([OH:33])=[O:13])=[O:30]

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 57446831HCID 57446831, compound

Product 1

HCID 18448167HCID 18448167, compoundYield 92.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4.2 g of 4-bromobutyl (2Z)-4-hydroxy-2-[4-(methylsulfonyl)phenyl]-3-phenylbut-2-en-1-yl carbonate in 50 mL of dichloromethane was treated with 4.2 g of Dess-Martin reagent for 1 h at rt. The reaction was quenched by 0.5 mL of water and stirred at rt for 1 h, filtered, and evaporated. The residue was dissolved in a solvent mixture of 30 mL of THF and 30 mL of t-BuOH, and treated with 50 mL of 1 M of H3PO4 and 25 mL of 1 M of NaClO2 in the presence of 5 mL of 2-methyl-2-butene. The resulting mixture was stirred at rt for 15 min; the organic layer was separated, washed with brine, dried (Na2SO4), and evaporated to afford 4 g of the crude acid for further use.

Workup

  1. customThe reaction was quenched by 0.5 mL of water
  2. filtrationfiltered
  3. customevaporated
  4. dissolutionThe residue was dissolved in a solvent mixture of 30 mL of THF and 30 mL of t-BuOH
  5. additiontreated with 50 mL of 1 M of H3PO4 and 25 mL of 1 M of NaClO2 in the presence of 5 mL of 2-methyl-2-butene
  6. stirringThe resulting mixture was stirred at rt for 15 min
  7. customthe organic layer was separated
  8. washwashed with brine
  9. dry with materialdried (Na2SO4)
  10. customevaporated

Sources & evidence

ORD record
ord-8515052c8a474bbea824509fbc9dbfa2
Source dataset
uspto-grants-2007_04
Patent number
US07199154B2

Reaction notes

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