HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triethylamine → Diethyl(E)-2-{-4-[cycloheptylidene(4-hydroxyphenyl)methyl]phenyl}ethenylphosphonate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Diethyl vinylphosphonate | HCID 69629 | — |
| Reactant | Tri-o-tolylphosphine | HCID 80271 | — |
| Reactant | 4-[(4-Bromophenyl)(cycloheptylidene)methyl]phenol | HCID 68654125 | — |
| Reactant | tert-Butyl (2E)-3-{4-[(4-hydroxyphenyl)(tetrahydro-4H-pyran-4-ylidene)methyl]phenyl}prop-2-enoate | HCID 86613505 | — |
| Catalyst | palladium(II) acetate | HCID 167845 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | Diethyl(E)-2-{-4-[cycloheptylidene(4-hydroxyphenyl)methyl]phenyl}ethenylphosphonate | HCID 86613508 | 28% |
Reaction Steps
Following the procedure described for compound 47, from 4-[(4-bromophenyl)cycloheptylidene)methyl]phenol (9) (0.146 g, 0.409 mmole), diethyl vinylphosphonate (0.190 mL, 1.24 mmole), P(o-tolyl)3 (0.0123 g, 0.0404 mmole), Et3N (0.170 mL, 1.22 mmole), Pd(OAc)2 (0.0046 g, 0.0205 mmole) and DMF (1.5 mL) yielded 63 (0.0502 g, 28%) as a white solid. 1H NMR (DMSO-d6): δ 9.28 (s, 1H), 7.57 (d, J=8.3 Hz, 2H), 7.30 (dd, J=22.7, 17.6 Hz, 1H), 7.11 (d, J=8.3 Hz, 2H), 6.89 (d, J=8.4 Hz, 2H), 6.65 (d, J=8.4 Hz, 2H), 6.48 (dd, J=22.7, 17.6 Hz, 1H), 4.01-3.91 (m, 4H), 2.20 (m, 4H), 1.50 (m, 8H), 1.21 (m, 6H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07799828B2 |
| Source dataset | uspto-grants-2010_09 |
| ORD ID | ord-66eb735f490244939f69774f92e4bb10 |
| Source note | uspto-grants-2010_09 |