Reaction #164430

Reaction equation

Acetate

(E)-(5-Bromo-6-{2-[2-(2-fluoroethoxy)ethoxy]ethoxy}pyridin-3-yl)-2-(4-acetoxyphenyl)-ethylene

K2CO3

→

11e

Yield 97.0%

(E)-(5-Bromo-6-{2-[2-(2-fluoroethoxy)ethoxy]ethoxy}pyridin-3-yl)-2-(4-hydroxyphenyl)-ethylene

Yield 97.0%

Solvents

EtOH THF

Conditions

Workup

1. 1
   Other2 h
2. 2
   OtherAfter standard workup with EtOAc, the crude product was purified by PTLC

Procedure

Acetate 11d (0.145 g, 0.31 mmol) and K2CO3 (0.064 g, 0.465 mmol) were placed in EtOH/THF (5 mL/5 mL) and the reaction mixture was stirred at r.t. 2 h. After standard workup with EtOAc, the crude product was purified by PTLC to give 11e as a white solid (0.128 g, 97%). 1H NMR δ8.07 (d, 1H, J=2.1 Hz), 7.99 (d, 1H, J=2.1 Hz), 7.35 (d, 2H, J=8.6 Hz), 6.96-6.74 (m, 4H), 5.22 (br s, 1H), 4.69 (t, 1H, J=4.2 Hz), 4.54 (t, 2H, J=4.8 Hz), 4.45 (t, 1H, J=4.2 Hz), 3.94-3.68 (m, 8H). 13C NMR δ 158.5, 156.4, 143.6, 138.2, 129.2, 129.0, 127.9, 120.7, 116.0, 107.6, 84.9, 81.6, 71.1, 71.0, 70.8, 70.4, 69.6, 66.8. HRMS calcd for C19H21BrFNO4 (M+), 425.0638; found, 425.0651.

Source