Sodium Thiosulfate → 2-(3,4-Dimethoxyphenyl)-2-methylpropanal

HRID 641856

Reaction equation

HRID 641856 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]([CH3:15])([CH3:14])[CH2:12][OH:13])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.C(=O)(O)[O-].[Na+].S([O-])([O-])(=O)=S.[Na+].[Na+]>ClCCl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]([CH3:15])([CH3:14])[CH:12]=[O:13])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

6

Reactant 4

HCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 130157782-(3,4-Dimethoxyphenyl)-2-methylpropan-1-ol

Product 1

HCID 592591132-(3,4-Dimethoxyphenyl)-2-methylpropanal

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 100 mg (0.476 mmol) 2-(3,4-dimethoxy-phenyl)-2-methyl-propan-1-ol in 1 ml dichloromethane is treated with 202 mg (0.476 mmol) Dess-Martin reagent at rt. After 1 h aqueous sodium bicarbonate and sodium thiosulphate solutions are added and the product is extracted with dichloromethane. The organic layers are evaporated and the aldehyde is obtained in a sufficient purity to be used in reductive aminations.

Workup

  1. extractionthe product is extracted with dichloromethane
  2. customThe organic layers are evaporated

Sources & evidence

ORD record
ord-dddd08e6850b4021b07f404df645263b
Source dataset
uspto-grants-2010_04
Patent number
US07696216B2

Linked notes

Loading…