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

HRID 2379525

Reaktionsgleichung

[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]

Komponenten

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

stirringThe cloudy yellow mixture was stirred at 20° C. for 2 hours
customquenched with saturated NH4Cl solution
washThe resulting mixture was washed with water
customdried
filtrationfiltered
customevaporated
customto give the crude product which
customwas purified by flash chromatography on a silica gel column
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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