Dimethyl Sulfoxide → 2,2'-Cyclopropane-1,1-diyldiacetaldehyde

Temperature

-50 °C

7.0 ml (79.9 mmol) of oxalyl chloride were dissolved in 45 ml of abs. dichloromethane, the mixture was cooled to −50° C. and a solution of 10.9 ml (163.6 mmol) of DMSO in 45 ml of abs. dichloromethane was added dropwise. After the end of the addition, the mixture was stirred at −50° C. for another 10 min, and 4.0 g (30.7 mmol) of 2,2′-cyclopropane-1,1-diyldiethanol, dissolved in 45 ml of abs. dichloromethane, were then added slowly. The resulting suspension was stirred at −50° C. for 10 min and then cooled to −78° C., and a solution of 44.5 ml (320 mmol) of triethylamine in 75 ml of abs. dichloromethane was added dropwise. After the end of the addition, the reaction mixture was stirred at −78° C. for 30 min and then slowly warmed to RT and subsequently washed with saturated aqueous sodium bisulphate solution. The organic phase was dried over sodium sulphate and concentrated under reduced pressure. This gave 5.10 g of the target product as an orange oil (crude product of a purity of about 70%, about 92% of theory).

1. additionAfter the end of the addition
2. stirringThe resulting suspension was stirred at −50° C. for 10 min
3. temperaturecooled to −78° C.
4. additionAfter the end of the addition
5. stirringthe reaction mixture was stirred at −78° C. for 30 min
6. temperatureslowly warmed to RT
7. washsubsequently washed with saturated aqueous sodium bisulphate solution
8. dry with materialThe organic phase was dried over sodium sulphate
9. concentrationconcentrated under reduced pressure

ORD record

ord-9cc10f6d483f496f987efd53ed41a9e6

Source dataset

uspto-grants-2016_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09309198B2