Reaction #55870

Reaction equation

thiophene

trichloroacetaldehyde

water

→

trichloroacetaldehyde isopropyl alcoholate

Solvents

methylene chloride

methylene chloride

Conditions

Workup

1. 1
   workup.STIRRINGwith stirring and under ice-water cooling
2. 2
   workup.ADDITIONAfter the addition
3. 3
   workup.STIRRINGstirring
4. 4
   workup.WAITwas continued for further 10 min.
5. 5
   Otherthe organic layer was separated
6. 6
   WashThe organic layer was washed with water
7. 7
   Dryingdried over anhydrous magnesium sulfate
8. 8
   FiltrationThe solution was filtered
9. 9
   Otherafter removal of the solvent
10. 10
    workup.DISTILLATIONby distillation under a reduced pressure with an aspirator
11. 11
    workup.DISTILLATIONthe residue was distilled

Procedure

To a solution of titanium tetrachloride in methylene chloride (1 molar concentration; 30 ml, 30 mmol), titanium tetraisopropoxide (4.26 g, 15 mmol) was added under an argon atmosphere with stirring and under water cooling. After 10 min., thiophene (2.52 g, 30 mmol) was added and then trichloroacetaldehyde (8.82 g, 60 mmol) was added dropwise during 10 min. with stirring and under ice-water cooling. After the addition was completed, stirring was continued for further 10 min., and then water and methylene chloride were added successively, and the organic layer was separated. The organic layer was washed with water and dried over anhydrous magnesium sulfate. The solution was filtered and, after removal of the solvent by distillation under a reduced pressure with an aspirator, the residue was distilled to form trichloroacetaldehyde isopropyl alcoholate initially and then 5.0 g of α-trichloromethyl-2-thiophenemethanol.

Source