Reaction #69999

Reaction equation

MEM-Cl

(E)-3-(3′-adamantan-1-yl-4′-hydroxybiphenyl-4-yl)-acrylic acid methyl ester

NaH

water

→

(E)-3-[3′-adamantan-1-yl-4′-(2-methoxyethoxymethoxy)-biphenyl-4-yl]-acrylic acid methyl ester

Yield 84.0%

Solvents

DMF

DMF

Conditions

Workup

1. 1
   workup.STIRRINGAfter stirring overnight at RT
2. 2
   Extractionthe mixture was extracted several times with EtOAc
3. 3
   DryingThe combined organic phases were dried over Na2SO4
4. 4
   Filtrationfiltered
5. 5
   Concentrationconcentrated under vacuo
6. 6
   OtherThe resulting crude product was purified on silica gel (acetone:hexane 15:85)

Procedure

A solution of (E)-3-(3′-adamantan-1-yl-4′-hydroxybiphenyl-4-yl)-acrylic acid methyl ester (120 mg, 0.309 mmol) in 1 ml of anhydrous DMF, was dropped into a 1 ml suspension of NaH (14.8 mg, 0.371 mmol, 60% in mineral oil) in anhydrous DMF (0.3 ml) at 0° C. The resulting red solution was stirred at RT for 30 min, then MEM-Cl (46 mg, 0.371 mmol) was added. After stirring overnight at RT, iced water was added and the mixture was extracted several times with EtOAc. The combined organic phases were dried over Na2SO4, filtered and concentrated under vacuo. The resulting crude product was purified on silica gel (acetone:hexane 15:85) to obtain (E)-3-[3′-adamantan-1-yl-4′-(2-methoxyethoxymethoxy)-biphenyl-4-yl]-acrylic acid methyl ester (123 mg, 84%).

Source