HuagongsheHuagongshe Chemistry Print Report · For research reference only
tert-Butyl (2E)-3-{4-[(4-hydroxyphenyl)(tetrahydro-4H-pyran-4-ylidene)methyl]phenyl}-2-methylprop-2-enoate → (2E)-3-{4-[(4-hydroxyphenyl)(tetrahydro-4H-pyran-4-ylidene)methyl]phenyl}-2-methylprop-2-enoic acid
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | tert-Butyl (2E)-3-{4-[(4-hydroxyphenyl)(tetrahydro-4H-pyran-4-ylidene)methyl]phenyl}-2-methylprop-2-enoate | HCID 86613507 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Solvent | Trifluoroacetic acid | HCID 6422 | — |
| Product | (2E)-3-{4-[(4-hydroxyphenyl)(tetrahydro-4H-pyran-4-ylidene)methyl]phenyl}-2-methylprop-2-enoic acid | HCID 11268134 | 47.8% |
Reaction Steps
tert-Butyl (2E)-3-{4-[(4-hydroxyphenyl)(tetrahydro-4H-pyran-4-ylidene)methyl]phenyl}-2-methylprop-2-enoate (59) (0.0702 g, 0.173 mmole) was dissolved in CH2Cl2 (1 mL) and TFA (1 mL). The solution was stirred at RT for 4 h, then was concentrated. The residue was triturated with CH2Cl2 to provide compound 60 (0.029 g, 47%) as a tan solid. 1H NMR (DMSO-d6): δ 12.49 (br s, 1H), 9.38 (s, 1H), 7.54 (s, 1H), 7.40 (d, J=8.1 Hz, 2H), 7.11 (d, J=8.1 Hz, 2H), 6.87 (d, J=8.4 Hz, 2H), 6.68 (d, J=8.4 Hz, 2H), 3.60 (m, 4H), 2.25 (m, 4H), 2.01 (s, 3H). LRMS (ESI): m/z 349 (M−H)−.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07799828B2 |
| Source dataset | uspto-grants-2010_09 |
| ORD ID | ord-e62c5afc1e44482cbb1b0ba745734bde |
| Source note | uspto-grants-2010_09 |