HuagongsheHuagongshe Chemistry Print Report · For research reference only
Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl ester → 3-Methyl-hept-2-enedioic acid dimethyl ester, E
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl ester | HCID 70670 | — |
| Reactant | Pentanoic acid, 5-oxo-, methyl ester | HCID 554053 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | 3-Methyl-hept-2-enedioic acid dimethyl ester, E | HCID 6429588 | 48% |
Reaction Steps
A solution of methyl 5-oxopentanoate (1.9 g, 14.6 mmol) and (carboethoxymethylene) triphenylphosphorane (5.0 g, 14.9 mmol) in toluene (50 mL) was refluxed for 8 hours. Solvent was removed under vacuo and the crude was purified by flash chromatography on silica gel (eluant: AcOEt/hexane 2/8) to give 1.32 g (48% yield) as colorless oil of the title compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09309253B2 |
| Source dataset | uspto-grants-2016_04 |
| ORD ID | ord-8c98136f68ea4e76ae873c363dfc477e |
| Source note | uspto-grants-2016_04 |