Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | Ammonium Chloride | HCID 25517 | — |
| Reactant | HCID 57708991 | HCID 57708991 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 57708944 | HCID 57708944 | 100% |
Reaction Steps
Sodium hydride (60% in oil, 8.4 mg, 0.209 mmol) was added to tetrahydrofuran (1 mL) at 0° C. Triethyl phosphonoacetate (0.049 mL, 0.244 mmol) and then a solution of 5-[4-(1-{4-[3-(t-butyl-dimethyl-silanyloxy)-4,4-dimethyl-pentyl]-3-methyl-phenyl}-1-ethyl-propyl)-2-methyl-phenyl]-furan-2-carbaldehyde (Example 3-(6); 100 mg, 0.174 mmol) in tetrahydrofuran (0.6 mL) were added at the same temperature, and the mixture was stirred for 20 minutes. A saturated aqueous ammonium chloride solution and ethyl acetate were added to the reaction mixture. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by a silica gel column (hexane only to hexane/ethyl acetate=9/1) to give the title compound (112 mg, 100%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US07935688B2 |
|---|
| Source dataset | uspto-grants-2011_05 |
|---|
| ORD ID | ord-68551b0194834dd2a66ba8fb8425ac64 |
|---|
| Source note | uspto-grants-2011_05 |
|---|