Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Formic Acid | HCID 284 | — |
| Reactant | 3,3-Dimethylbutanal | HCID 76335 | — |
| Reactant | HCID 86656548 | HCID 86656548 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 58392798 | HCID 58392798 | 27.7% |
Reaction Steps
In a closed vessel, compound 166 (180 mg, 0.391 mmol), 3,3-dimethylbutanal (0.196 ml, 1.565 mmol) and TEA (0.055 ml, 0.391 mmol) are dissolved in acetonitrile (4 ml). Formic acid (0.120 ml, 3.13 mmol) is added and the mixture is heated under microwave irradiation for 15 minutes at 140° C. LC-MS shows that the reaction is complete. The reaction mixture is diluted with AcOEt and the organic phase is washed with a saturated solution of NaHCO3 and with brine. The organic layer is dried over Na2SO4 and filtered. The solvent is evaporated to give an orange oil which is purified by preparative HPLC (acetonitrile/water, neutral phase) to yield the title compound (55 mg, 0.108 mmol, 27.7% yield).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08481517B2 |
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| Source dataset | uspto-grants-2013_07 |
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| ORD ID | ord-05bc13c3c6684ea696e1e66230d5ba65 |
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| Source note | uspto-grants-2013_07 |
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