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Sodium hydride → Dimethyl [1-acetyl-4,8,12-trimethyltrideca-3,7,11-trienyl]phosphonate

HRID 2379525
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2379525
[O:1]=[C:2]([CH3:10])[CH2:3][P:4](=[O:9])([O:7][CH3:8])[O:5][CH3:6].[H-].[Na+].[CH2:13](Br)[CH:14]=[C:15]([CH2:17][CH2:18][CH:19]=[C:20]([CH2:22][CH2:23][CH:24]=[C:25]([CH3:27])[CH3:26])[CH3:21])[CH3:16]>C1COCC1>[C:2]([CH:3]([P:4](=[O:9])([O:7][CH3:8])[O:5][CH3:6])[CH2:13][CH:14]=[C:15]([CH3:16])[CH2:17][CH2:18][CH:19]=[C:20]([CH3:21])[CH2:22][CH2:23][CH:24]=[C:25]([CH3:27])[CH3:26])(=[O:1])[CH3:10]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 77872Dimethyl (2-oxopropyl)phosphonateHCID 550199Farnesyl bromide

Produkt 1

HCID 53770837Dimethyl [1-acetyl-4,8,12-trimethyltrideca-3,7,11-trienyl]phosphonate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

Dimethyl 2-oxopropylphosphonate (560 μL, 4.0 mmol) was added dropwise to a stirred suspension of sodium hydride (50% oil suspension, prewashed with hexane) (210 mg, 4.8 mmol) in anhydrous THF (15 mL) at 20° C. under an Argon atmosphere. The resulting slurry was stirred at 20° C. for 2 hours to allow for complete formation of the sodio derivative and then treated dropwise with farnesyl bromide (1.14 mL, 4.2 mmol). The cloudy yellow mixture was stirred at 20° C. for 2 hours and then quenched with saturated NH4Cl solution. The resulting mixture was washed with water, dried, filtered and evaporated to give the crude product which was purified by flash chromatography on a silica gel column. Elution of the column with hexane:ethyl acetate:methanol (40:10:1, v:v:v) gave the title compound as gum.

Aufarbeitung

  1. stirringThe cloudy yellow mixture was stirred at 20° C. for 2 hours
  2. customquenched with saturated NH4Cl solution
  3. washThe resulting mixture was washed with water
  4. customdried
  5. filtrationfiltered
  6. customevaporated
  7. customto give the crude product which
  8. customwas purified by flash chromatography on a silica gel column
  9. washElution of the column with hexane:ethyl acetate:methanol (40:10:1, v:v:v)

Quellen und Nachweise

ORD-Eintrag
ord-d5939e86e2d841549056d7ee8dc6dc37
Quelldatensatz
uspto-grants-1994_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05362906

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