HuagongsheHuagongshe Chemistry Print Report · For research reference only
Water → (3Z)-(5S)-5,9-Dimethyl-dec-3-ene-1,9-diol
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Hydrofluoric Acid | HCID 14917 | — |
| Reactant | (Z)-(S)-1-(t-Butyl-dimethyl-silanyloxy)-5,9-dimethyl-9-triethylsilanyloxy-dec-3-ene | HCID 57680486 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | (3Z)-(5S)-5,9-Dimethyl-dec-3-ene-1,9-diol | HCID 57680494 | 95.3% |
Reaction Steps
To a stirred solution of compound 12 (201 mg, 0.4 mmol) in anhydrous CH2Cl2 (10 mL) was added hydrofluoric acid (48%, 6 mL). After 40 minutes of stirring at room temperature, water was added, and the organic layer was separated, washed with water and NaHCO3, dried over MgSO4, and evaporated. The residue was chromatographed on silica Sep-Pak cartridge using hexane/EtOAc (6:4) as an eluent to give an oily diol 13 (76.4 mg, 92%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07534777B2 |
| Source dataset | uspto-grants-2009_05 |
| ORD ID | ord-7f4287cc60bc46afa4e8955e4e93c629 |
| Source note | uspto-grants-2009_05 |