Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Benzothiazole | HCID 7222 | — |
| Reactant | Tetrahydrofuran | HCID 8028 | — |
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | Butyllithium | HCID 178418339 | — |
| Product | Bis(2-methylphenyl)methanone | HCID 219387 | 64% |
Reaction Steps
Step 5 Under anhydrous conditions the benzothiazole acid (step 4) was dissolved in THF (0.052 M). At −78° C. added BuLi (2.2 eq). After 1 h at −78° C. to 0° C., added the amide (1.28 eq) from step 1 of Example 81, in THF, at −78° C., over 5 min. After 0.5 h at −78° C., the reaction was allowed to warm to 25° C. After stirring at 25° C. for 2 h, workup with ethyl acetate and water and chromatography afforded pure tolyl ketone acid product (64%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US06916841B2 |
|---|
| Source dataset | uspto-grants-2005_07 |
|---|
| ORD ID | ord-5399eb0d3fe44e1399b865a426fdc97c |
|---|
| Source note | uspto-grants-2005_07 |
|---|