HuagongsheHuagongshe Chemistry Print Report · For research reference only
Methanol → (1R)-1-(2-chlorophenyl)ethan-1-ol
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Methanol | HCID 887 | — |
| Reactant | Ethanone, 1-(2-chlorophenyl)- | HCID 72864 | — |
| Reactant | (3aS)-1-methyl-3,3-diphenyl-hexahydropyrrolo(1,2-c)(1,3,2)oxazaborole | HCID 2734713 | — |
| Reactant | (Dimethyl sulfide)trihydroboron | HCID 12423031 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | (1R)-1-(2-chlorophenyl)ethan-1-ol | HCID 6999092 | — |
Reaction Steps
2′-Chloroacetophenone (8.4 mL, 65 mmol) and (S)-(−)-2-methyl-CBS-oxazaborolidine (0.90 g, 0.32 mmol) were combined in THF (75 mL). Borane methyl sulfide complex (2M in THF; 21.5 mL, 43 mmol) was added over 20 minutes, and the reaction was stirred at room temperature for 30 minutes. MeOH was added, and the mixture was worked-up with CH2Cl2 and H2O. The organic layer was concentrated to give the title compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08048902B2 |
| Source dataset | uspto-grants-2011_11 |
| ORD ID | ord-e196a10a0a71453aaaddf8f00d28a16f |
| Source note | uspto-grants-2011_11 |