Reaktionsgleichung
[H-].[Na+].[CH2:3]1[CH2:7][O:6][CH2:5][CH2:4]1.[O:8]1[CH2:12][CH2:11][CH:10]([CH:13]=O)[CH2:9]1.CN(C=[O:19])C>O>[O:6]1[CH2:7][CH2:3][CH:4](/[CH:13]=[CH:10]/[C:9]([O:8][CH2:12][CH3:11])=[O:19])[CH2:5]1Komponenten
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
To a 0° C. mixture of sodium hydride (60% in mineral oil) (382 mg, 9.40 mmol) in DMF (15.0 mL) (THF may also be used) was added triethyl phosphonoacetate (1.72 mL, 8.68 mmol) dropwise. The resulting mixture was warmed to room temperature and stirred for 30 minutes, then was re-cooled to 0° C., at which time a solution of tetrahydrofuran-3-carbaldehyde (724 mg, 7.23 mmol) in DMF (4.0 mL) was added dropwise. The resulting mixture was stirred at this temperature for 1.5 hours, at which time the mixture was diluted with water and the product was extracted with ether. The combined extracts were washed with water and brine, dried over sodium sulfate and the solvent removed in vacuo. Flash column chromatography (eluting with a gradient from 0-40% ethyl acetate in hexanes) afforded the product (640 mg, 52%).
Aufarbeitung
- additionwas added dropwise
- stirringThe resulting mixture was stirred at this temperature for 1.5 hours, at which time the mixture
- extractionthe product was extracted with ether
- washThe combined extracts were washed with water and brine
- dry with materialdried over sodium sulfate
- customthe solvent removed in vacuo
- washFlash column chromatography (eluting with a gradient from 0-40% ethyl acetate in hexanes)
Quellen und Nachweise
- ORD-Eintrag
- ord-0e0e5abbebe245e5bdff0726e8491b93
- Quelldatensatz
- uspto-grants-2009_10
- Patentnummer
- US07598257B2
Verknüpfte Notizen
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