Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Tributylphosphine | HCID 13831 | — |
| Reactant | 1,1'-(Azodicarbonyl)dipiperidine | HCID 73042 | — |
| Reactant | 2-(Methylthio)ethanol | HCID 78925 | — |
| Reactant | HCID 66777135 | HCID 66777135 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 66777532 | HCID 66777532 | 76% |
Reaction Steps
Cyclohexyl(5-hydroxy-3-methyl-1-benzofuran-2-yl)methanone (0.76 g) synthesized in Example A82(3) was dissolved in tetrahydrofuran (15 mL), and 2-(methylthio)ethanol (0.26 mL), tributylphosphine (1.5 mL) and 1,1′-(azodicarbonyl)dipiperidine (1.46 g) were added to the solution under ice-cooling. The ice bath was removed, and the reaction mixture was stirred at room temperature for 12 hr. Hexane (15 mL) was added to the mixture, and the precipitate was filtered off through celite. Water was added to the filtrate, and the mixture was extracted with ethyl acetate. The extract was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:4, volume ratio) to give the title object compound (0.73 g, 76%) as a pale-yellow oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08436043B2 |
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| Source dataset | uspto-grants-2013_05 |
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| ORD ID | ord-bac6445a30854b3e8b91fe8fcdd1490c |
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| Source note | uspto-grants-2013_05 |
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