Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Tributylphosphine | HCID 13831 | — |
| Reactant | 1,1'-(Azodicarbonyl)dipiperidine | HCID 73042 | — |
| Reactant | Ethyl 3-(3,5-difluoro-4-hydroxyphenyl)propanoate | HCID 23136305 | — |
| Reactant | HCID 90406977 | HCID 90406977 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | HCID 90406160 | HCID 90406160 | 46.2% |
Reaction Steps
Into a 50-mL round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed [1-phenyl-3-(trifluoromethyl)-1H-pyrrol-2-yl]methanol (260 mg, 1.05 mmol, 1.00 equiv, 97%), ethyl 3-(3,5-difluoro-4-hydroxyphenyl)propanoate (281 mg, 1.22 mmol, 1.20 equiv), ADDP (642 mg, 2.56 mmol, 2.50 equiv), Bu3P (309 mg, 1.53 mmol, 1.50 equiv) and toluene (5 mL). The resulting solution was stirred overnight at 60° C. in an oil bath. The resulting mixture was then concentrated under vacuum. The resulting mixture was washed with diethyl ether (50 mL). The resulting residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:5) to yield ethyl 3-(3,5-difluoro-4-[[1-phenyl-3-(trifluoromethyl)-1H-pyrrol-2-yl]methoxy]phenyl)propanoate as yellow oil (220 mg, 45%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09045454B2 |
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| Source dataset | uspto-grants-2015_06 |
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| ORD ID | ord-90679e7c68d54d4492ca9db4d9e1b7b7 |
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| Source note | uspto-grants-2015_06 |
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