HuagongsheHuagongshe Chemistry Print Report · For research reference only
Benzaldehyde → (R,R)-Stilbene oxide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Benzaldehyde | HCID 240 | — |
| Reactant | Benzene, (diazomethyl)- | HCID 136601 | — |
| Reactant | HCID 178418361 | HCID 178418361 | — |
| Catalyst | Acetic acid, rhodium(2+) salt | HCID 21674 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Solvent | tert-Butyl methyl ether | HCID 15413 | — |
| Product | (R,R)-Stilbene oxide | HCID 185583 | 5% |
Reaction Steps
A solution of phenyldiazomethane (0.45 mmol in 6 ml of t-butylmethyl ether was added to a solution of a compound of formula (C') wherein R' and R" are both hydrogen (90 mg; 0.45 mmol), rhodium (II) acetate (2 mg; 0.0045 mmol) and benzaldehyde (46 μl; 0.45 mmol) in dichloromethane (2 ml). Upon completion of the addition, the solvent was removed in vacuo and the residue chromatographed using silica gel and elating with dichloromethane:petrol 40:60 to give the title compound (4 mg, 5%, 71%ee).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US05703246 |
| Source dataset | uspto-grants-1997_12 |
| ORD ID | ord-8c5f22bc875a4d278e0a450db37cc256 |
| Source note | uspto-grants-1997_12 |