Réaction #2487467

Équation de réaction

tert-butyl (5-chloro-4-methoxy-2-methylphenyl)carbamate

sec-butyllithium

tetrahydrofuran

tetrahydrofuran

ammonium chloride

water

→

title compound

tert-Butyl[5-chloro-2-(2-hydroxy-3-methylpentyl)-4-methoxyphenyl]carbamate

Conditions de réaction

Traitement

1. 1
   workup.STIRRINGthe mixture was stirred at −45° C. for 35 minutes
2. 2
   workup.STIRRINGstirred at room temperature for 90 more minutes
3. 3
   Extractionfollowed by extraction with ethyl acetate
4. 4
   LavageThe organic layer was washed with saturated brine
5. 5
   Séchagedried over anhydrous sodium sulfate
6. 6
   Concentrationconcentrated under reduced pressure
7. 7
   AutreThe residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane)

Mode opératoire

Under an argon atmosphere, to a solution of tert-butyl (5-chloro-4-methoxy-2-methylphenyl)carbamate (1.00 g) in tetrahydrofuran (18.4 mL) was added dropwise sec-butyllithium (1.08 mol/L hexane-cyclohexane solution, 7.5 mL) at −45° C., and the mixture was stirred for 30 minutes. Next, a solution of 2-methylbutyl aldehyde (0.430 mL) in tetrahydrofuran (1.84 mL) was added dropwise thereto, and the mixture was stirred at −45° C. for 35 minutes and then stirred at room temperature for 90 more minutes. To the reaction mixture was added saturated aqueous ammonium chloride solution/water (3/1, 40 mL), followed by extraction with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane) to obtain the title compound (876 mg). 1H-NMR (CDCl3) δ ppm: 0.50-2.30 (19H, m), 2.45-2.95 (2H, m), 3.55-4.05 (4H, m), 6.60-6.80 (1H, m), 7.20-8.00 (2H, m).

Source