Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | HCID 21914412 | HCID 21914412 | — |
| Reactant | Butyllithium | HCID 178418339 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Solvent | Hexane | HCID 8058 | — |
| Product | HCID 86033953 | HCID 86033953 | — |
Reaction Steps
A solution of Intermediate 28 (895 mg) in anhydrous THF (10 ml) was added dropwise with a 1.6 M solution of n-butyllithium in hexane (2.70 ml, Ald) over 5 minutes with cooling at −78° C. under argon gas atmosphere, and stirred for 20 minutes. This reaction mixture was added with dehydrated DMF (330 μl, WAKO) over 3 minutes, stirred for 30 minutes, then warmed to room temperature, and further stirred for 1 hour. The reaction mixture was added with water (10 ml), and extracted with ethyl acetate (30 ml×3). The organic layer was washed with saturated brine and dried, and then the solvent was evaporated under reduced pressure. The residue was purified by column chromatography (Quad, hexane:ethyl acetate=10:1) to obtain the title compound (Intermediate 29, 1.04 g).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US07470807B2 |
|---|
| Source dataset | uspto-grants-2008_12 |
|---|
| ORD ID | ord-54ede4ed7d8b44539ac78c7e97efd00c |
|---|
| Source note | uspto-grants-2008_12 |
|---|