Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Furfural | HCID 7362 | — |
| Reactant | Diethyl Carbonate | HCID 7766 | — |
| Reactant | Diisopropylamine | HCID 7912 | — |
| Reactant | Tetrahydrofuran | HCID 8028 | — |
| Reactant | Butyllithium | HCID 178418339 | — |
| Solvent | Hexane | HCID 8058 | — |
| Product | HCID 67088637 | HCID 67088637 | — |
Reaction Steps
In the next step, n-butyllithium (2.15 equivalents) in hexane was cooled to −70° C. and diisopropylamine (2.25 equivalents) was added while keeping the temperature below −60° C. Compound 1″ (1 equivalent) dissolved in tetrahydrofuran (THF) was added over 30 min at −70° C. After 10 min, diethyl carbonate (1.05 equivalents) dissolved in THF was added over 30 min keeping the reaction temperature below −60° C. After stirring for one hour at −60° C., the reaction was allowed to warm to 15° C. and furan-2-carbaldehyde (1.3 equivalents) dissolved in THF was added. After stirring for 20 hrs at room temperature, the reaction was rotary evaporated to dryness to yield ethyl 2-(1,3-dioxolan2-yl)methyl-3-(furan-2-yl)acrylate, compound 5″. Crude compound 5″ was used directly in the next reaction.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08378105B2 |
|---|
| Source dataset | uspto-grants-2013_02 |
|---|
| ORD ID | ord-ce5d3fb5222a41f5b656b436dfc4ba27 |
|---|
| Source note | uspto-grants-2013_02 |
|---|