Reaction #554570

Reaction equation

Trityl chloride

14a

Methyl 6-hydroxy-hexanoate

→

orange oil 15a

Yield 86.3%

Methyl 6-trityloxy-hexanoate

Yield 86.3%

Solvents

pyridine

Conditions

Workup

1. 1
   Otherformed
2. 2
   OtherThe solvent was removed under reduced pressure
3. 3
   workup.DISSOLUTIONthe resulting material was redissolved in ice cold THF
4. 4
   OtherThe insoluble byproduct was removed by filtration
5. 5
   Otherthe filtrate was dried under reduced pressure

Procedure

Trityl chloride (18.8 g, 67.4 mmol) was added to an ice cold (0° C.) stirring solution of 14a (9.9 g, 67.4 mmol) in 80 mL of pyridine. The reaction mixture was warmed to room temperature and stirred under argon for 2 days, during which time a white byproduct formed. The solvent was removed under reduced pressure, and the resulting material was redissolved in ice cold THF. The insoluble byproduct was removed by filtration, and the filtrate was dried under reduced pressure to obtain 22.6 g (86%) of an orange oil 15a. 1H-NMR (400 MHz, CDCl3, δH ppm): 7.43 (6H, m, p-Ar), 7.29 (6, m, m-Ar), 7.22 (3H, m, o-Ar), 3.65 (3H, s, CO2CH3), 3.05 (2H, t, 3JH—H=6.6 Hz, HO—CH2), 2.29 (2H, t, 3JH—H=7.5 Hz, CH2CO2), 1.54-1.71 (4H, m, 2CH2), 1.33-1.45 (m, 2H, CH2). HRMS (EI): m/z calcd 388.2038 (C26H28O3), found 388.2039 [M]+.

Source