Acetaldehyde → 1-[2-methyl-7-(2,4,6-trimethyl-phenyl)-2H-indazol-3-yl]-ethanol

HRID 902548

Reaktionsgleichung

[CH3:1][N:2]1[CH:10]=[C:9]2[C:4]([C:5]([C:11]3[C:16]([CH3:17])=[CH:15][C:14]([CH3:18])=[CH:13][C:12]=3[CH3:19])=[CH:6][CH:7]=[CH:8]2)=[N:3]1.C([N-]C(C)C)(C)C.[Li+].[O:28]1CC[CH2:30][CH2:29]1.CCCCCCC.C(C1C=CC=CC=1)C.C(=O)C>C1COCC1>[CH3:1][N:2]1[C:10]([CH:29]([OH:28])[CH3:30])=[C:9]2[C:4]([C:5]([C:11]3[C:16]([CH3:17])=[CH:15][C:14]([CH3:18])=[CH:13][C:12]=3[CH3:19])=[CH:6][CH:7]=[CH:8]2)=[N:3]1

Komponenten

Reaktionsbedingungen

Temperatur: 2.5 °C

Versuchsvorschrift

To a solution of the above-prepared impure 2-methyl-7-(2,4,6-trimethyl-phenyl)-2H-indazole (0.500 g) in 10 mL of THF at −78° C. was added a 2.0 M solution of lithium diisopropylamide in tetrahydrofuran/heptane/ethylbenzene (1.2 mL, 2.4 mmol). The yellow solution was stirred at 0-5° C. for 15 m, and the resulting purple solution rechilled to −78° C. for 15 m. Acetaldehyde (0.14 mL, 2.5 mmol) was added, and the resulting yellow solution was stirred for 90 m then quenched with silica gel and concentrated. Column chromatography (0→50% EtOAc/hexanes) afforded of 1-[2-methyl-7-(2,4,6-trimethyl-phenyl)-2H-indazol-3-yl]-ethanol (12a: R=Me, R′=2,4,6-trimethylphenyl, E=CH(OH)Me; 0.280 g; 48%; m.p. 246) as a white solid.

Aufarbeitung

customrechilled to −78° C. for 15 m
stirringthe resulting yellow solution was stirred for 90 m
customthen quenched with silica gel
concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag: ord-005e8901e939492eb645ad67b8a3683c
Quelldatensatz: uspto-grants-2008_04
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07365211B2

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