Sodium Thiosulfate → HCID 11160483, compound

HRID 2215265Notes

Reaction equation

HRID 2215265 reaction equation
[CH3:1][O:2][C@H:3]([CH2:6][S:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[O:14][CH3:15])[CH2:4][OH:5].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.S([O-])([O-])(=O)=S.[Na+].[Na+].C(=O)([O-])O.[Na+]>ClCCl>[CH3:1][O:2][C@H:3]([CH2:6][S:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[O:14][CH3:15])[CH:4]=[O:5]

Participants

6

Reactant 4

HCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 69652629HCID 69652629, compound

Product 1

HCID 11160483HCID 11160483, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4 g (0.017 mol) of 2-(S)-methoxy-3-(2-methoxyphenylthio)propan-1-ol (XIV-1), 100 ml of dichloromethane and 11.13 g (0.026 mol) of Dess-Martin reagent are introduced into a round-bottomed flask kept under an inert atmosphere. The mixture is stirred at ambient temperature for 3 hours. 190 ml of a saturated aqueous sodium thiosulfate solution are subsequently added, followed by 190 ml of a saturated aqueous sodium hydrogencarbonate solution, and the mixture is extracted with dichloromethane. The combined organic phases are washed with water and with brine, dried over magnesium sulfate, filtered and concentrated under reduced pressure. The residue is purified by flash chromatography on silica gel (eluent: dichloromethane/ethyl acetate=95:5). 1.2 g (0.005 mol) of the title compound (IIa-1) are recovered in the form of a yellow oil.

Workup

  1. extractionthe mixture is extracted with dichloromethane
  2. washThe combined organic phases are washed with water and with brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue is purified by flash chromatography on silica gel (eluent: dichloromethane/ethyl acetate=95:5)

Sources & evidence

ORD record
ord-89e79f7d0de14afca7e405be46e553f4
Source dataset
uspto-grants-2006_09
Patent number
US07109234B2

Reaction notes

Loading…