HuagongsheHuagongshe Chemistry Print Report · For research reference only
Oxygen → 5-t-Butyl-1-(4-hydroxy-2-phenylbenzo[d]oxazol-6-yl)-4,4-dimethyl-2,6,7-trioxabicyclo[3.2.0]heptane
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Oxygen | HCID 977 | — |
| Reactant | Sodium | HCID 5360545 | — |
| Reactant | 4-t-Butyl-5-(4-hydroxy-2-phenylbenzo[d]oxazol-6-yl)-3,3-dimethyl-2,3-dihydrofuran | HCID 15547440 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | 5-t-Butyl-1-(4-hydroxy-2-phenylbenzo[d]oxazol-6-yl)-4,4-dimethyl-2,6,7-trioxabicyclo[3.2.0]heptane | HCID 9800824 | 85.1% |
Reaction Steps
To 15 mL of methylene chloride were added 1.0 mg of TPP and 156 mg (0.43 mmol) of 4-t-butyl-5-(4-hydroxy-2-phenylbenzo[d]oxazol-6-yl)-3,3-dimethyl-2,3-dihydrofuran (Compound [63]), and the mixture was externally irradiated with a 940 W sodium lamp in an oxygen atmosphere for 30 minutes, then concentrated. The concentrate was applied to a silica gel column and the elution was carried out with the mixture of hexane and ethyl acetate (hexane:ether =1:1) to obtain 25.3 mg of 5-t-butyl-1-(4-hydroxy-2-phenylbenzo[d]oxazol-6-yl)-4,4-dimethyl-2,6,7-trioxabicyclo[3.2.0]heptane (Compound [64]) as colorless granular crystal. Yield 85.1%.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06218135B1 |
| Source dataset | uspto-grants-2001_04 |
| ORD ID | ord-c6a65e81e5fe44029ea42f7b304f4597 |
| Source note | uspto-grants-2001_04 |