Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Lithium Hydroxide | HCID 3939 | — |
| Reactant | Diethyl (cyanomethyl)phosphonate | HCID 75676 | — |
| Reactant | HCID 58007939 | HCID 58007939 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 67442988 | HCID 67442988 | 70% |
Reaction Steps
A mixture of lithium hydroxide (101 mg, 2.40 mmol), diethyl cyanomethylphosphonate (390 mg, 2.20 mmol) and tetrahydrofuran (20 ml) was stirred at 70° C. for 30 minutes under argon atmosphere. After the reaction mixture was cooled to room temperature, 4-[4-(tert-butyl)benzyloxy]-4′-(trifluoromethoxy)biphenyl-3-carbaldehyde (compound of Example 4 (2); 857 mg, 2.00 mmol) was added, and the mixture was stirred at room temperature for 4 hours. 1N Hydrochloric acid was added to the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The residue obtained by evaporation of the solvent under reduced pressure was purified by column chromatography on silica gel (n-hexane:ethyl acetate=10:1) to give the title compound (631 mg, 70.0%) as a colorless oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08044236B2 |
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| Source dataset | uspto-grants-2011_10 |
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| ORD ID | ord-b8b4788c684341afa39f3fb0170866fb |
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| Source note | uspto-grants-2011_10 |
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