Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Acetyl chloride | HCID 6367 | — |
| Reactant | Ammonium Chloride | HCID 25517 | — |
| Reactant | Magnesium Chloride | HCID 5360315 | — |
| Reactant | Ethyl 4-t-butoxyacetoacetate | HCID 11790264 | — |
| Solvent | Pyridine | HCID 1049 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 85826160 | HCID 85826160 | — |
Reaction Steps
A suspension of dry magnesium chloride (0.471 g) in dichloromethane (6 ml) was treated with 4-tert-butoxy-3-oxo-butyric acid ethyl ester [1.00 g, Reference Example 43]. This mixture was cooled to 0° C., then treated with pyridine (0.80 ml), then stirred for 15 minutes at 0° C. and then treated with acetyl chloride (0.352 ml). After stirring for a further 15 minutes at 0° C. and then for 1 hour at ambient temperature the reaction mixture was treated with saturated aqueous ammonium chloride solution and then extracted twice with ethyl acetate. The combined extracts were dried over magnesium sulfate and then evaporated to yield 2-acetyl-4-tert-butoxy-3-oxo-butyric acid ethyl ester (1.15 g) as a yellow oil which was used without further purification. LC-MS (METHOD B): RT=3.16 minutes; 243 (M−H)−.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08288425B2 |
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| Source dataset | uspto-grants-2012_10 |
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| ORD ID | ord-911552e7b9464f0991adb0a205215e01 |
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| Source note | uspto-grants-2012_10 |
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