Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Methanol | HCID 887 | — |
| Reactant | Water | HCID 962 | — |
| Reactant | Diisobutylaluminum hydride | HCID 14487 | — |
| Reactant | HCID 21989703 | HCID 21989703 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | HCID 86673381 | HCID 86673381 | 94.2% |
Reaction Steps
To a solution of (E)-ethyl 3-(4-(diethoxymethyl)phenyl)acrylate (1.400 g) in toluene (10 mL) was added DIBAH (1 M solution in toluene) (10 mL) at −20° C. under an Ar atmosphere. The mixture was stirred at −20° C. for 1 hour. To the mixture was added MeOH, and then the mixture was heated to room temperature. To the mixture was added water, and the mixture was extracted with AcOEt. The organic layer was washed with saturated aqueous NaCl, dried over anhydrous Na2SO4, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane/AcOEt=1/1) to afford (E)-3-[4-(diethoxymethyl)phenyl]prop-2-en-1-ol (1.120 g) as a colorless oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08722663B2 |
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| Source dataset | uspto-grants-2014_05 |
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| ORD ID | ord-f0cb617da1ac438fa00b2a7576ef0c96 |
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| Source note | uspto-grants-2014_05 |
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