Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Hydrazine hydrate (1:1) | HCID 24654 | — |
| Reactant | Methyl 4-oxobutyrate | HCID 83779 | — |
| Reactant | (5-Methoxy-3-oxo-1,3-dihydro-isobenzofuran-1-yl)triphenyl phosphonium bromide | HCID 11562468 | — |
| Solvent | Ethanol | HCID 702 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 12109280 | HCID 12109280 | 75.7% |
Reaction Steps
A solution of 3-formyl-propionic acid methyl ester (13.4 g, 0.1155 moles) and (5-methoxy-3-oxo-1,3-dihydro-isobenzofuran-1-yl)-triphenyl-phosphonium bromide (55.6 g, 0.11 moles), prepared as described in example 36, in CH2Cl2 (440 ml) in water bath was dropwise added with triethylamine (16.1 ml, 0.1155 mole). At the end of the addition the mixture was stirred at room temperature overnight, then washed with water, anhydrified and dried to give a residue which was taken up in ethanol (180 ml). The solution was cooled and added with hydrazine monohydrate (11 g, 0.22 mole). A precipitate formed and was filtered. After 6 days the mother liquors gave a precipitate which joined to the previous one yielded 23 g of the title compound (yield: 75.5%). m.p.: 175-177° C.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06492360B1 |
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| Source dataset | uspto-grants-2002_12 |
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| ORD ID | ord-ba2a5430f43d43a4a7bc8e4eb6d5ec33 |
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| Source note | uspto-grants-2002_12 |
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