Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Diethyl Ether | HCID 3283 | — |
| Reactant | Ammonium Chloride | HCID 25517 | — |
| Reactant | HCID 86604735 | HCID 86604735 | — |
| Reactant | HCID 178418365 | HCID 178418365 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 67050265 | HCID 67050265 | 34% |
Reaction Steps
To a solution of 2-(4-t-butylphenyl)-3-methoxymethyloxy-4-formylthiophene (3.0 g, 10 mmol) in THF (2.5 mL), 2.0 M ethyl ether solution (6.0 mL, 12 mmol) of isopropylmagnesium bromide was added dropwise under cooling with ice, followed by stirring for 2.5 hours under cooling with ice. A saturated ammonium chloride aqueous solution was added to the reaction solution, and then extraction was carried out with ethyl acetate, and the organic layer was washed with a saturated sodium chloride solution and then dried over anhydrous sodium sulfate. The obtained organic layer was concentrated, and then purification was carried out with a silica gel column chromatography (n-hexane/ethyl acetate=3/1) to obtain the desired product as a pale yellow oil (1.18 g, yield 34%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08318796B2 |
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| Source dataset | uspto-grants-2012_11 |
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| ORD ID | ord-bbf09568caae48cdb004b49cd9ea3a6a |
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| Source note | uspto-grants-2012_11 |
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