Dimethyl (2-oxopropyl)phosphonate → methyl(3E)-2,2-dimethyl-5-oxohex-3-enoate

HRID 928094

Reaktionsgleichung

Reaktionsgleichung von HRID 928094
[O:1]=[C:2]([CH3:10])[CH2:3]P(=O)(OC)OC.CC(C)([O-])C.[K+].[CH3:17][C:18]([CH3:25])([CH:23]=O)[C:19]([O:21][CH3:22])=[O:20]>O1CCCC1>[CH3:17][C:18]([CH3:25])(/[CH:23]=[CH:3]/[C:2](=[O:1])[CH3:10])[C:19]([O:21][CH3:22])=[O:20]

Komponenten

5

Edukt 3

HCID 77872Dimethyl (2-oxopropyl)phosphonateHCID 11137194Methyl 2,2-dimethyl-3-oxopropanoateHCID 23665647Potassium tert-butoxide

Produkt 1

HCID 86658242methyl(3E)-2,2-dimethyl-5-oxohex-3-enoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of dimethyl (2-oxopropyl)phosphonate (4.09 mL, 30.0 mmol) in tetrahydrofuran (200 mL) at 0° C. was added potassium tert-butoxide (3.22 g, 28.7 mmol). After 15 minutes the reaction mixture was moved to room temperature, and after an additional 15 minutes methyl 2,2-dimethyl-3-oxopropanoate (3.39 g, 26.0 mmol) was added. The opaque reaction mixture was stirred for 21 hours and then partitioned between diethyl ether (100 ml) and water (100 mL). The layers were separated and the aqueous layer was extracted with diethyl ether (100 mL, 50 mL). The combined organic layers were washed with aqueous saturated sodium bicarbonate solution and brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by chromatography on silica gel (0-4% methanol/dichloromethane) to yield methyl (3E)-2,2-dimethyl-5-oxohex-3-enoate. 1H NMR (500 MHz, CDCl3) δ 6.95 (d, J=16.4 Hz, 1H), 6.09 (d, J=16.4 Hz, 1H), 3.71 (s, 3H), 2.29 (s, 3H), 1.37 (s, 6H).

Aufarbeitung

  1. customThe opaque reaction mixture
  2. custompartitioned between diethyl ether (100 ml) and water (100 mL)
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted with diethyl ether (100 mL, 50 mL)
  5. washThe combined organic layers were washed with aqueous saturated sodium bicarbonate solution and brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by chromatography on silica gel (0-4% methanol/dichloromethane)

Quellen und Nachweise

ORD-Eintrag
ord-5330b7fbae544dc9a6a3f103f25d0cbd
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09290490B2

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