Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Sodium Hydroxide | HCID 14798 | — |
| Reactant | (2Z,4E,6E)-2,6-difluoro-3-methyl-7-(5,5,8,8-tetramethyl-3-propoxy-5,6,7,8-tetrahydro-naphthalen-2-yl)-octa-2,4,6-trienoic acid ethyl ester | HCID 12146419 | — |
| Solvent | Ethanol | HCID 702 | — |
| Product | HCID 10388100 | HCID 10388100 | 73% |
Reaction Steps
To a solution of (2Z,4E,6E)-2,6-difluoro-3-methyl-7-(5,5,8,8-tetramethyl-3-propoxy-5,6,7,8-tetrahydro-naphthalen-2-yl)-octa-2,4,6-trienoic acid ethyl ester (Compound 10, 82 mg, 0.18 mmol) in EtOH (2 mL) was added 1M NaOH (1.0 mL). The mixture was heated to 60° C. for 2 h and was cooled to ambient temperature, acidified with 1M HCl, and extracted with EtOAc (×3). The combined organic layer was washed with brine, dried over Na2SO4, and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel (50% EtOAc-hexane) to give the title compound as a pale yellow solid (56 mg, 73%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06759547B1 |
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| Source dataset | uspto-grants-2004_07 |
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| ORD ID | ord-91b6ab371c2744079bd8cdf87f73c26e |
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| Source note | uspto-grants-2004_07 |
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