Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylsilane | HCID 12052 | — |
| Reactant | (R)-S-Ethyl 2-(2,2-dimethyl-5-oxo-1,3-dioxolan-4-yl)ethanethioate | HCID 53627664 | — |
| Catalyst | Palladium | HCID 23938 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 24864236 | HCID 24864236 | 87.2% |
Reaction Steps
To a stirred suspension of (R)—S-ethyl 2-(2,2-dimethyl-5-oxo-1,3-dioxolan-4-yl)ethanethioate (1.9 g, 8.7 mmol), 10% palladium on carbon (470 mg), and CH2Cl2 (20 mL) under N2, at 25° C., was added triethylsilane (2.08 mL, 13.0 mmol) dropwise over 10 minutes. The mixture was stirred at 25° C. for 1 hour. The mixture was filtered and the filtrate was evaporated to dryness under reduced pressure to give the desired aldehyde as a clear oil (1.2 g, 87%). 1H-NMR (400 MHz, CDCl3) δ 9.70 (s, 1H), 4.72 (q, J=3.5 Hz, 1H), 3.10-3.01 (m, 1H), 2.93-2.84 (m, 1H), 1.56 (s, 3H), 1.51 (s, 3H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08143297B2 |
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| Source dataset | uspto-grants-2012_03 |
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| ORD ID | ord-ec8c3b710d724332999d9775c23fe7f7 |
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| Source note | uspto-grants-2012_03 |
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