1-Fluoro-2-iodobenzene → 8-(2-Fluorophenyl)-1,4-dioxaspiro[4.5]decan-8-ol

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Reaktionsgleichung

[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1I.C([Li])CCC.[CH2:14]1[O:24][C:17]2([CH2:22][CH2:21][C:20](=[O:23])[CH2:19][CH2:18]2)[O:16][CH2:15]1.C(=O)(O)[O-].[Na+]>C1COCC1>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:20]1([OH:23])[CH2:21][CH2:22][C:17]2([O:24][CH2:14][CH2:15][O:16]2)[CH2:18][CH2:19]1

Komponenten

Reaktionsbedingungen

Temperatur: -78 °C

Versuchsvorschrift

To a solution of 2-fluoro-1-Iodobenzene (11.1 g, 50.0 mmol) in 50 mL THF, cooled to −78° C. under argon, was added n-butyllithium (20.0 mL 2.5M in hexane, 50.0 mmol). The solution was stirred 10 min. at −78° C., and a solution of 1,4-cyclohexanedione mono-ethylene ketal (7.81 g, 50.0 mmol) in 50 mL THF was added slowly. The solution was warmed to r.t. and stirred for 60 min., then poured onto saturated sodium bicarbonate and extracted with ethylacetate. The combined organic layers were washed with saturated sodium chloride, dried with magnesium sulfate, and concentrated in vacuo. The crude solid was crystallized from dichloromethane/hexane to give 8-(2-Fluoro-phenyl)-1,4-dioxa-spiro-[4.5]decan-8-ol (3.8 g, 30%).

Aufarbeitung

temperatureThe solution was warmed to r.t.
stirringstirred for 60 min.
extractionextracted with ethylacetate
washThe combined organic layers were washed with saturated sodium chloride
dry with materialdried with magnesium sulfate
concentrationconcentrated in vacuo
customThe crude solid was crystallized from dichloromethane/hexane

Quellen und Nachweise

ORD-Eintrag: ord-c118451cc169486e90e3685de2868454
Quelldatensatz: uspto-grants-2001_07
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US06255315B1

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