HuagongsheHuagongshe Chemistry Print Report · For research reference only
Hydrochloric Acid → (S)-5-(2-Hydroxyethyl)-2,2-dimethyl-1,3-dioxolan-4-one
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | (S)-2-(2,2-Dimethyl-5-oxo-1,3-dioxolan-4-yl)acetic acid | HCID 641720 | — |
| Reactant | Borane;tetrahydrofuran | HCID 2723981 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | (S)-5-(2-Hydroxyethyl)-2,2-dimethyl-1,3-dioxolan-4-one | HCID 10975778 | 73.2% |
Reaction Steps
Step B To the solution of ((S)-2,2-dimethyl-5-oxo-[1,3]dioxolan-4-yl)-acetic acid (10.1 g, 58 mmol) in anhydrous tetrahydrofuran (20 mL) at 0° C. was added a solution of BH3.THF (1 M, 70 mL, 70 mmol). The reaction mixture was stirred at room temperature for 2 h. Aqueous HCl solution was added, and the mixture was extracted with ethyl acetate. The organic layer was separated, washed with saturated aqueous NaHCO3 solution, brine, dried over MgSO4, and concentrated. The residue was purified by chromatography (EtOAc) to give (S)-5-(2-hydroxy-ethyl)-2,2-dimethyl-[1,3]dioxolan-4-one as a colorless oil (6.8 g, 72%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08354444B2 |
| Source dataset | uspto-grants-2013_01 |
| ORD ID | ord-f0ac5cf4d03d4e7eb878379d092a0e42 |
| Source note | uspto-grants-2013_01 |