Reaction #311928

Reaction equation

(1R,cis)-2-(2,2-dimethoxyethyl)-3,3-dimethylcyclopropanecarbaldehyde

carbon tetrachloride

water

Tri(dimethylamino)phosphine

→

residue

Yield 94.7%

(1R,cis)-2-[2-(2,2-dichlorovinyl)-3,3-dimethylcyclopropyl]ethanal dimethyl acetal

Yield 94.7%

Solvents

n-pentane

Conditions

Workup

1. 1
   Otherkept under nitrogen in a 1-l flask
2. 2
   workup.WAITkept at this temperature for 15 minutes
3. 3
   Other--after removal of the aqueous phase
4. 4
   Washthe organic phase was washed with two 35-ml portions of water
5. 5
   DryingThe washed organic phase was dried over anhydrous magnesium sulphate
6. 6
   Otherthe solvent was evaporated from the dried solution

Procedure

Tri(dimethylamino)phosphine (163.2 mmol) was added with stirring at 0° C. to a solution of (1R,cis)-2-(2,2-dimethoxyethyl)-3,3-dimethylcyclopropanecarbaldehyde (65.5 mmol) and carbon tetrachloride (163.2 mmol) in n-pentane (350 ml) kept under nitrogen in a 1-l flask. After 15 minutes stirring, the mixture was warmed up to 14° C. and kept at this temperature for 15 minutes. Then, water (75 ml) was added at 14° C. and--after removal of the aqueous phase--the organic phase was washed with two 35-ml portions of water. The washed organic phase was dried over anhydrous magnesium sulphate and the solvent was evaporated from the dried solution to give a residue (15.7 g) containing 32.1 mmol of 2-[2-(2,2-dichlorovinyl)-3,3-dimethylcyclopropyl]ethanal dimethyl acetal (100% (1R,cis), purity 51.7%, yield 49%).

Source