Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Pentanal | HCID 8063 | — |
| Reactant | HCID 23378642 | HCID 23378642 | — |
| Reactant | Butyllithium | HCID 178418339 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Solvent | Hexamethylphosphoramide | HCID 12679 | — |
| Product | HCID 22671994 | HCID 22671994 | 40.8% |
Reaction Steps
To a solution of 2-(N-isopropyl-methylsulfonylamino)-5-trifluoromethyl-phenyl methoxymethyl ether (135 mg; prepared in Reference Example 30.) in THF (3.0 ml), hexamethylphosphoramide (420 μl) was added in a stream of argon. At −78° C., n-butyl lithium (742 μl) was added dropwise thereto. The mixture was stirred for 1.5 hours. To the mixture, a solution of valeraldehyde (102 mg) in THF (1.0 ml) was added dropwise. The mixture was stirred for 30 minutes. To the reaction mixture, water was added. The mixture was extracted with ethyl acetate, washed, dried over and concentrated with the reduced pressure. The residue was purified on silica gel column chromatography (hexane:AcOEt=4:1) to give the title compound (69 mg) having the following physical data.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US06790866B2 |
|---|
| Source dataset | uspto-grants-2004_09 |
|---|
| ORD ID | ord-cb98667288d84b5190064b38ccda73bd |
|---|
| Source note | uspto-grants-2004_09 |
|---|