Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Imidazole | HCID 795 | — |
| Reactant | Water | HCID 962 | — |
| Reactant | Phthalide | HCID 6885 | — |
| Reactant | tert-Butyldimethylsilyl chloride | HCID 28928 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Hexane | HCID 8058 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 69142436 | HCID 69142436 | 94% |
Reaction Steps
tert-Butylchlorodimethylsilane (647.3 mg, 4.30 mmol) and imidazole (292.3 mg, 4.30 mmol) were added to 6-(hydroxymethyl)-[(3H)-isobenzofuranone (587.5 mg, 3.58 mmol) obtained from Example 1-(4) or Example 1-(6) in N,N-dimethylformamide (10 ml). After the mixture was stirred at room temperature for 1 hour, water (20 ml) was added thereto, and then the product was extracted with a mixed solvent of ethyl acetate and hexane. The organic layer was washed with water and then with a saturated aqueous solution of sodium chloride, and the solvent was distilled off under reduced pressure to afford an oily residue. The residue was subjected to chromatography on a silica gel (25 g) column (eluent; ethyl acetate:hexane=1:10˜1:1) to give the title compound (940.1 mg, 94% yield) as a colorless oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07230023B2 |
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| Source dataset | uspto-grants-2007_06 |
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| ORD ID | ord-3d9a9570a3674683b69386ff682d259b |
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| Source note | uspto-grants-2007_06 |
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