HuagongsheHuagongshe Chemistry Print Report · For research reference only
Potassium Carbonate → (R*,S*)-(+/-)-5-(2-(5-(3-chlorophenyl)-2-oxo-3-oxazolidinyl)propyl)-1,3-benzodioxole-2,2-dicarboxylic acid, diethyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | Propanedioic acid, 2,2-dibromo-, 1,3-diethyl ester | HCID 69427 | — |
| Reactant | (R*,S*)-(+/-)-5-(3-chlorophenyl)-3-(2-(3,4-dihydroxyphenyl)-1-methylethyl)-2-oxazolidinone | HCID 67823889 | — |
| Catalyst | Propanedioic acid, 2,2-dibromo-, 1,3-diethyl ester | HCID 69427 | — |
| Solvent | Acetone | HCID 180 | — |
| Product | (R*,S*)-(+/-)-5-(2-(5-(3-chlorophenyl)-2-oxo-3-oxazolidinyl)propyl)-1,3-benzodioxole-2,2-dicarboxylic acid, diethyl ester | HCID 15669208 | 66.1% |
Reaction Steps
A mixture of 0.8 g of the above oxazolidinone, 0.74 g of diethyl dibromomalonate, 1.2 g of anhydrous potassium carbonate and 20 ml of acetone are stirred overnight with the addition of a few drops of diethyl dibromomalonate. The mixture is filtered, washed with acetone and the combined filtrate and wash are evaporated to a yellow oil. The oil is purified by flash chromatography, eluting with 5 percent acetone in toluene. The pure fractions are combined and evaporated, giving 766 mg of (R*,S*)-(±)-5-(2-(5-(3-chlorophenyl)-2-oxo-3-oxazolidinyl)propyl)-1,3-benzodioxole-2,2 -dicarboxylic acid, diethyl ester as a colorless oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US05373020 |
| Source dataset | uspto-grants-1994_12 |
| ORD ID | ord-e50a558e7cb948cdac49929c20b4c4ae |
| Source note | uspto-grants-1994_12 |