Reaction #162038

Reaction equation

Cholestanol

Potassium tert-butoxide

tert-Butyl bromoacetate

→

product

Yield 76.0%

tert-Butyl 2-(cholestan-3-yloxy)acetate

Yield 76.0%

Solvents

toluene

Toluene

Conditions

Workup

1. 1
   workup.STIRRINGthe mixture was stirred overnight at room temperature
2. 2
   Washthe solution was washed with brine (50 mL)
3. 3
   ExtractionThe aqueous phase was extracted with toluene (30 mL) before all organic phases
4. 4
   Dryingdried (Na2SO4)
5. 5
   Otherthe solvent evaporated
6. 6
   OtherThe crude product was purified

Procedure

Cholestanol (0.662 g, 1.703 mmol) was dissolved in toluene (13 mL). Potassium tert-butoxide (573 mg, 5.11 mmol) was added in one portion. The mixture was stirred at room temperature for 3 hours. tert-Butyl bromoacetate (503 μL, 3.406 mmol) was added drop-wise and the mixture was stirred overnight at room temperature. Toluene (20 mL) was added and the solution was washed with brine (50 mL). The aqueous phase was extracted with toluene (30 mL) before all organic phases were combined, dried (Na2SO4) and the solvent evaporated. The crude product was purified using column chromatography (SiO2; Hexane:EtOAc, 200:1 to 200:20) to yield the white solid product (0.65 g, 76% yield). 1H NMR (400 MHz, CDCl3) δ: 3.98 (s, 2H, CH2O), 3.30 (m, 1H, CHO), 1.97-0.56 (m, 31H), 1.46 (s, 9H, CH3), 0.89 (d, 3H, J=6.1, CH3), 0.85 (d, 3H, J=2.0, CH3), 0.84 (d, 3H, J=1.4, CH3), 0.79 (s, 3H, CH3), 0.64 (s, 3H, CH3).

Source