Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Tetrahydrofuran | HCID 8028 | — |
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | Ethyl diethoxyacetate | HCID 80169 | — |
| Reactant | Ethyl 3-oxohexanoate | HCID 238498 | — |
| Reactant | Butyllithium | HCID 178418339 | — |
| Product | HCID 54720306 | HCID 54720306 | 53% |
Reaction Steps
A solution of sodium hydride (60% dispersion in mineral oil) in tetrahydrofurane (500 ml) was cooled at 0° C. under nitrogen. 3-oxo-hexanoic-acid ethyl ester (25 g; 158 mmol) was added dropwise and the mixture was stirred at 0° C. for 15 minutes. Butyllithium 1.6 M (99 ml; 158 mmol) was added dropwise and the mixture was stirred at 0° C. for 1 hour. Diethoxy-acetic acid ethyl ester (27.8 g; 0.178 mol) was added drop wise and the mixture was stirred at 0° C. for 1 hour. Hydrochloric acid 12 N (50 ml) was added and the mixture was stirred at room temperature for 1 hour and extracted with diethyl ether to yield 20 g (53%) of intermediate 19. The product was used without further purification in the next reaction step.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07115608B2 |
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| Source dataset | uspto-grants-2006_10 |
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| ORD ID | ord-4170be9b5e6c4ccfb38b721bb54f036d |
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| Source note | uspto-grants-2006_10 |
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