Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | HCID 57789077 | HCID 57789077 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Solvent | Cyclohexane | HCID 8078 | — |
| Product | HCID 86652435 | HCID 86652435 | 30.2% |
Reaction Steps
1 g (1.46 mmol) 2,8-di-(triphenylsilyl)-dibenzofuran are dissolved in 100 ml dry THF at 45° C. and 10 ml of 1.4 M sec-Buthyllithium solution in cyclohexane is added. After stirring for 15 min. at 45° C., 2 ml of dry DMF is added; the reaction mixture is stirred for 1 h. 100 ml of 0.5 M HCl is added to quench the reaction. The product is extracted with ethylacetate and purified by column chromatography on silica gel with heptane:ethylacetate (3:1) as an eluent. 2,8-di-(triphenylsilyl)-dibenzofuran-4-carboxaldehyde (5.3) is obtained in 30.2% yield.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08685541B2 |
|---|
| Source dataset | uspto-grants-2014_04 |
|---|
| ORD ID | ord-8b7ad890decf4837b63a30d7eb78c575 |
|---|
| Source note | uspto-grants-2014_04 |
|---|