HuagongsheHuagongshe Chemistry Print Report · For research reference only
Dimethyl Sulfoxide → 1-[(4-Methylphenyl)sulfonyl] 2-pyrrolidinecarboxaldehyde
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Dimethyl Sulfoxide | HCID 679 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Oxalyl chloride | HCID 65578 | — |
| Reactant | 1-tosyl-2-(S)-pyrrolidinemethanol | HCID 724414 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | 1-[(4-Methylphenyl)sulfonyl] 2-pyrrolidinecarboxaldehyde | HCID 15614172 | — |
Reaction Steps
To a stirred solution of 5 g (0.0394 mol) of oxalyl chloride in 50 ml of CH2Cl2 at -60° is added dropwise 7 g (0.0833 mol) of DMSO. The solution is stirred 30 minutes at -60° and then 10 g (0.039 mol) of N-tosylprolinol is added over five minutes at 60° and 15 ml of triethylamine is added. The solution is warmed to 25° and stirred one hour. The solution is then washed with H2O, dried over MgSO4 and the solvents removed. The residual oil, 10 g, is purified using a silica gel column and CHCl3 :MeOH (90:10) as the eluates. An oil is obtained which solidifies, 9.5 g (96%), mp 139°-140°.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US04596819 |
| Source dataset | uspto-grants-1986_06 |
| ORD ID | ord-789c7be106c64206a3fcfcdd22831508 |
| Source note | uspto-grants-1986_06 |