Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium Sulfate | HCID 24436 | — |
| Reactant | lithium aluminium hydride THF | HCID 68718528 | — |
| Reactant | HCID 86616385 | HCID 86616385 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 86616384 | HCID 86616384 | 74% |
Reaction Steps
The above-obtained [2-(N-benzylcarbamoyl)-6-ethyl-3,5-bis(methoxymethoxy)phenyl]acetic acid methyl ester (46 mg, 0.11 mmol) was dissolved in tetrahydrofuran (5 mL) and cooled to 0° C. The obtained solution was added with 1.0 mol/L lithium aluminum hydride-tetrahydrofuran solution (0.20 mL, 0.20 mmol) followed by stirring at 0° C. for 0.5 hour. The reaction mixture was added with saturated aqueous sodium sulfate solution, and was extracted with ethyl acetate 3 times. The organic layers were combined, washed with saturated brine, dried over anhydrous sodium sulfate and then the solvent was evaporated under reduced pressure. The residue was purified by preparative thin-layer chromatography (hexane/ethyl acetate=1/1) to obtain N-benzyl-3-ethyl-2-(2-hydroxyethyl)-4,6-bis(methoxymethoxy)benzamide (30 mg, 74%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07781485B2 |
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| Source dataset | uspto-grants-2010_08 |
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| ORD ID | ord-b4fa4359d2694b399e82322baf6bdb79 |
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| Source note | uspto-grants-2010_08 |
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