HuagongsheHuagongshe Chemistry Print Report · For research reference only
Methanol → (1R,4S)-4-hydroxy-cyclopent-2-ene-1,2-dicarboxylic acid 2-methyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Methanol | HCID 887 | — |
| Reactant | Toluene | HCID 1140 | — |
| Reactant | Lithium Hydroxide | HCID 3939 | — |
| Reactant | 4-Hydroxy-cyclopent-2-ene-1,2-dicarboxylic acid dimethyl ester | HCID 59165443 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | (1R,4S)-4-hydroxy-cyclopent-2-ene-1,2-dicarboxylic acid 2-methyl ester | HCID 68410381 | 27% |
Reaction Steps
To an ice-cold solution of compound 27 (3.4 g, 22 mmol) dissolved in dioxane and water (1:1, 110 mL), LiOH (0.52 g, 22 mmol) was added. After two and a half hours the mixture was co-evaporated with toluene and methanol. Purification by flash chromatography (toluene/Ethyl acetate 3:1+1% HOAc) gave the title compound (1.0 g, 27%) as yellow-white crystals.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07700552B2 |
| Source dataset | uspto-grants-2010_04 |
| ORD ID | ord-f915b318e0fe4668b64f4f222c518eb1 |
| Source note | uspto-grants-2010_04 |