反应 #1483141

ord-355744b5a2b347f697d82a0b3fe8db40

反应方程式

O=S(c1ccc(O)cc1)c1ccc(O)cc1
4,4′-sulfinyldiphenol
O=C([O-])[O-].[K+].[K+]
potassium carbonate
COCCOCCBr
1-bromo-2-(2-methoxyethoxy)ethane
COCCOCCOc1ccc(S(=O)c2ccc(OCCOCCOC)cc2)cc1
title compound
COCCOCCOc1ccc(S(=O)c2ccc(OCCOCCOC)cc2)cc1
4,4′-sulfinylbis((2-(2-methoxyethoxy)ethoxy)benzene)

反应条件

详细条件
See reaction.notes.procedure_details.

后处理

  1. 1
    温度the solution heated to 90° C. for 18 h
  2. 2
    温度cooled to r.t
  3. 3
    洗涤washed with water (5×500 mL)
  4. 4
    干燥dried (Na2SO4)
  5. 5
    浓缩concentrated in vacuo

实验过程

4,4′-sulfinyldiphenol (20.0 g, 85.0 mmol), potassium carbonate (26.6 g, 0.192 mol, 2.26 eq) and tetramethylethylenediamine (0.495 g, 4.25 mmol, 0.05 eq) were dissolved in DMSO (100 mL) and stirred at r.t. for 30 minutes. Then 1-bromo-2-(2-methoxyethoxy)ethane (32.67 g, 0.179 mmol, 2.1 eq) was added, the solution heated to 90° C. for 18 h and cooled to r.t. The reaction mixture was diluted with ethyl acetate (600 mL), washed with water (5×500 mL), dried (Na2SO4) and concentrated in vacuo to afford the title compound (33.40 g, 90%) as an orange oil. 1H NMR (500 MHz, (CD3)2CO) δ: 7.59 (d, J=8.5 Hz, 4H), 7.07 (d, J=8.5 Hz, 4H), 4.17 (t, J=4.5 Hz, 4H), 3.80 (t, J=5 Hz, 4H), 3.63 (t, J=4.5 Hz, 4H), 3.48 (t, J=4.5 Hz, 4H), 3.28 (s, 6H).

来源

DOI: 10.6084/m9.figshare.5104873.v1专利: US08900792B2uspto-grants-2014_12