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 90418044 | HCID 90418044 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | HCID 90418129 | HCID 90418129 | — |
Reaction Steps
Into a 25-mL round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed [5-(2-fluoro-4-methylphenyl)-3-methyl-1,2-thiazol-4-yl]methanol (100 mg, 0.42 mmol, 1.00 equiv), ethyl 3-(3,5-difluoro-4-hydroxyphenyl)propanoate (146 mg, 0.63 mmol, 1.50 equiv), ADDP (221.6 mg, 0.89 mmol, 2.10 equiv), Bu3P (128 mg, 0.63 mmol, 1.5 equiv), toluene (10 mL). The resulting solution was stirred overnight at 60° C. The resulting mixture was concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:5). This resulted in 150 mg (79%) of ethyl 3-(3,5-difluoro-4-[[5-(2-fluoro-4-methylphenyl)-3-methyl-1,2-thiazol-4-yl]methoxy]phenyl) propanoate as colorless oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09067898B1 |
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| Source dataset | uspto-grants-2015_06 |
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| ORD ID | ord-ea0bc50e0e604bbaa733d05f0bb9a4aa |
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| Source note | uspto-grants-2015_06 |
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