HuagongsheHuagongshe Chemistry Print Report · For research reference only
Methanol → (3,3-Dimethoxy-1-vinylcyclobutyl)methanol
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Methanol | HCID 887 | — |
| Reactant | Diisobutylaluminum hydride | HCID 14487 | — |
| Reactant | Methyl 3,3-dimethoxy-1-vinylcyclobutanecarboxylate | HCID 86724271 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | (3,3-Dimethoxy-1-vinylcyclobutyl)methanol | HCID 86724270 | 81.7% |
Reaction Conditions
| Temperature | 0 °C |
|---|
Reaction Steps
To a solution of methyl 3,3-dimethoxy-1-vinylcyclobutanecarboxylate (2.02 g, 10.09 mmol) in THF (20 mL) was added DIBAL-H (1.04M in toluene, 29 mL, 30.16 mmol) at 0° C. under argon, and the mixture was stirred for 30 minutes at 0° C. To the mixture was carefully added MeOH (29 mL) and Na2SO4.10H2O (29 g), and the mixture was stirred overnight. The mixture was filtered and evaporated under reduced pressure. And the residue was diluted with hexane/EtOAc=1:1 and filtrated through the pad of silica gel and concentrated in vacuo to give (3,3-dimethoxy-1-vinylcyclobutyl)methanol (1.42 g).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08975415B2 |
| Source dataset | uspto-grants-2015_03 |
| ORD ID | ord-06e198e7603f4d17ac1d6d4a422eaf0b |
| Source note | uspto-grants-2015_03 |