Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | 4-Hydroxycoumarin | HCID 54682930 | — |
| Reactant | HCID 58930721 | HCID 58930721 | — |
| Solvent | Formic Acid | HCID 284 | — |
| Product | HCID 58930724 | HCID 58930724 | — |
Reaction Steps
4-Hydroxycoumarin (1.367 g, 8.44 mmol) and (S)-4-formyl-benzoic acid 2,2,3,3,3-pentafluoro-1-methyl-propyl ester (2.505 g, 8.46 mmol) were dissolved in formic acid (3.0 mL) and Et3N (3.6 mL) at 0° C. After stirring at 140° C. for 4 h, the yellow solution was cooled to rt, EtOAc was added, and the organic layer was washed successively with 1 N HCl and brine. After drying over Na2SO4 and concentrating, the pale yellow solid was purified twice by silica gel chromatography (DCM:MeOH 100:6 and DCM:MeOH 100:5) to yield the title compound in 92.5% ee as determined by chiral HPLC.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07932405B2 |
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| Source dataset | uspto-grants-2011_04 |
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| ORD ID | ord-d3c176471795435080b8f748185de4d7 |
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| Source note | uspto-grants-2011_04 |
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