HuagongsheHuagongshe Chemistry Print Report · For research reference only
(2E)-3-{4-[Cyclohexylidene(4-hydroxyphenyl)methyl]phenyl}-2-propenamide → 4-[(4-Bromophenyl)(2,2,6,6-tetramethyltetrahydro-4H-pyran-4-ylidene)methyl]phenol
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | (2E)-3-{4-[Cyclohexylidene(4-hydroxyphenyl)methyl]phenyl}-2-propenamide | HCID 11256079 | — |
| Reactant | 2,2,6,6-Tetramethyloxan-4-one | HCID 11829691 | — |
| Reactant | 4-[(4-Bromophenyl)(tetrahydro-4H-pyran-4-ylidene)methyl]phenol | HCID 68654197 | — |
| Catalyst | Zinc | HCID 23994 | — |
| Catalyst | Titanium Tetrachloride | HCID 24193 | — |
| Product | 4-[(4-Bromophenyl)(2,2,6,6-tetramethyltetrahydro-4H-pyran-4-ylidene)methyl]phenol | HCID 68654325 | 76% |
Reaction Steps
Following the procedure described for compound 46, zinc powder (0.957 g, 14.6 mmole), TiCl4 (0.800 mL, 7.30 mmole), (4-bromophenyl)(4-hydroxyphenyl)methanone (2) (0.512 g, 1.85 mmole) and 2,2,6,6-tetramethyltetrahydro-4H-pyran-4-one (52) (0.851 mL, 5.45 mmole), afforded 0.564 g (76%) of 53 as a white foamy solid. 1H NMR (CDCl3): δ 7.41 (d, J=8.3 Hz, 2H), 7.02 (d, J=8.4 Hz, 2H), 7.01 (d, J=8.4 Hz, 2H), 6.76 (d, J=8.3 Hz, 2H), 4.99 (s, 1H), 2.24 (s, 2H), 2.20 (s, 2H), 1.22 (s, 6H), 1.21 (s, 6H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07799828B2 |
| Source dataset | uspto-grants-2010_09 |
| ORD ID | ord-63436bbf6112488a914d769c402d6c7d |
| Source note | uspto-grants-2010_09 |