Hexane → [4-Chloro-2-fluoro-5-methoxy-3-(trimethylsilyl)phenyl][4-(4-chlorophenoxy)-2-propylphenyl]methanol

HRID 1172825

Reaktionsgleichung

CC1(C)CCCC(C)(C)N1.C([Li])CCC.CCCCCC.[F:22][C:23]1[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[C:25]([Cl:31])[C:24]=1[Si:32]([CH3:35])([CH3:34])[CH3:33].[Cl:36][C:37]1[CH:54]=[CH:53][C:40]([O:41][C:42]2[CH:49]=[CH:48][C:45]([CH:46]=[O:47])=[C:44]([CH2:50][CH2:51][CH3:52])[CH:43]=2)=[CH:39][CH:38]=1.[Cl-].[NH4+]>C1COCC1>[Cl:31][C:25]1[C:26]([O:29][CH3:30])=[CH:27][C:28]([CH:46]([C:45]2[CH:48]=[CH:49][C:42]([O:41][C:40]3[CH:53]=[CH:54][C:37]([Cl:36])=[CH:38][CH:39]=3)=[CH:43][C:44]=2[CH2:50][CH2:51][CH3:52])[OH:47])=[C:23]([F:22])[C:24]=1[Si:32]([CH3:34])([CH3:33])[CH3:35]

Komponenten

Reaktionsbedingungen

Temperatur: -40 °C

Versuchsvorschrift

To a solution of 2,2,6,6-tetramethylpiperidine (2.75 g, 10 mmol) in THF (50 mL) cooled at −75° C. was added a solution of n-butyllithium in hexane (1.6 M, 6.3 mL, 10 mmol). After 15 min, 4-fluoro-2-chloro-3-(trimethylsilyl)anisole (2.3 g, 10 mmol) was added and the solution was warmed gradually to −40° C. over a 2 h period. The solution was recooled to −75° C. and a solution of the aldehyde from Step 1 of Example 3 (1.4 g, 5.0 mmol) in THF (3 mL) was added quickly. The reaction mixture was stirred for 15 min., poured into a saturated aqueous solution of ammonium chloride and extracted with ethyl acetate. After removal of the solvent, the residue was purified by chromatography on silica gel to give the title product.

Aufarbeitung

customwas recooled to −75° C.
extractionextracted with ethyl acetate
customAfter removal of the solvent
customthe residue was purified by chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag: ord-8ab7dbe4dfac470a9b7aa4d9fdbe6be1
Quelldatensatz: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07834036B2

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