Reacción #76592

Ecuación de reacción

ethyl 6-bromo-2-methyl-2-phenyl-hexanoate

thiourea

potassium hydroxide

→

6-(5-ethoxycarbonyl-5-phenylhexylsulfanyl)-2-methyl-2-phenyl-hexanoic acid ethyl ester

Rendimiento 85.0%

Disolventes

ethanol

Condiciones de reacción

Tratamiento posterior

1. 1
   ExtracciónThe mixture was extracted with dichloromethane (4′ 60 mL) and the combined organic layers
2. 2
   Lavadowere washed with sat. NaHCO3 solution (100 mL) and sat. NH4Cl solution (100 mL)
3. 3
   SecadoThe dichloromethane solution was dried over MgSO4
4. 4
   Concentraciónconcentrated in vacuo
5. 5
   OtroThe crude product was purified by column chromatography on silica gel (hexanes/ethyl acetate=10/1)

Procedimiento

A solution of ethyl 6-bromo-2-methyl-2-phenyl-hexanoate (18.5 g, 59.0 mmol), thiourea (7.0 g, 91.0 mmol), and potassium hydroxide (6.1 g, 92.0 mmol) in ethanol (200 mL) was heated to 40-50° C. overnight. The mixture was cooled to rt, poured into an ice/water/HCl mixture (150 g/150 mL/150 mL), and stirred for 20 min. The mixture was extracted with dichloromethane (4′ 60 mL) and the combined organic layers were washed with sat. NaHCO3 solution (100 mL) and sat. NH4Cl solution (100 mL). The dichloromethane solution was dried over MgSO4 and concentrated in vacuo. The crude product was purified by column chromatography on silica gel (hexanes/ethyl acetate=10/1) to give 6-(5-ethoxycarbonyl-5-phenylhexylsulfanyl)-2-methyl-2-phenyl-hexanoic acid ethyl ester (12.5 g, 85%) as a yellow oil. 1H NMR (300 MHz, CDCl3/TMS): d (ppm): 7.42-7.15 (m, 10H), 4.20-4.05 (q, 4H, J=7.1 Hz), 2.44 (t, J=7.6 Hz, 4H), 2.15-1.95 (m, 2H), 1.95-1.75 (m, 2H), 1.62-1.40 (m, 10H), 1.35-1.10 (m, 4H), 1.18 (t, 6H, J=7.1 Hz). 13C NMR (75 MHz, CDCl3/TMS): d (ppm): 176.06, 143.89, 128.25, 126.52, 125.84, 60.65, 50.04, 38.77, 31.80, 30.11, 24.06, 22.61, 14.01. HRMS (LSIMS, nba): Calcd. for C30H43O4S1 (MH+): 499.2882, found 499.2868.

Fuente