Reaction #51997

Reaction equation

oxalyl chloride

N2

DMSO

2-[methyl(trityl)amino]ethanol

Triethylamine

→

product

[Methyl(trityl)amino]acetaldehyde

Solvents

CH2Cl2

CH2Cl2

Conditions

Workup

1. 1
   OtherThe reaction was quenched
2. 2
   workup.ADDITIONby adding water
3. 3
   workup.ADDITIONdiluted with 100 mL of CH2Cl2
4. 4
   WashThe organic phase was washed with water and brine
5. 5
   Dryingdried over Na2SO4
6. 6
   Filtrationfiltered
7. 7
   Concentrationconcentrated in vacuo
8. 8
   OtherThe residue was triturated with ether

Procedure

A solution of DMSO (1.47 mL, 20.8 mmol) in 60 mL of CH2Cl2 was cooled to −78° C. and treated with oxalyl chloride dropwise under N2 atmosphere for 10 min. The resulting mixture was treated with a solution of 2-[methyl(trityl)amino]ethanol (3.0 g, 9.45 mmol) in 10 mL of CH2Cl2 dropwise and stirred for additional 15 min. Triethylamine (6.6 mL, 47.3 mmole) was added to the mixture and warmed up to room temperature. The reaction was quenched by adding water and diluted with 100 mL of CH2Cl2. The organic phase was washed with water and brine, dried over Na2SO4, filtered and concentrated in vacuo. The residue was triturated with ether to give the product as white solid.

Source