Potassium Carbonate → HCID 67608820, compound

HRID 1395959Notes

Reaction equation

HRID 1395959 reaction equation
[S:1]([C:10]1[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=1)([C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][CH:4]=1)=[O:2].[C:17](=[O:20])([O-])[O-].[K+].[K+].Br[CH2:24][CH2:25][O:26][CH2:27][CH2:28][O:29][CH3:30]>CS(C)=O.C(OCC)(=O)C.CN(C)CCN(C)C>[S:1]([C:10]1[CH:15]=[CH:14][C:13]([O:16][CH2:24][CH2:25][O:26][CH2:27][CH2:28][O:20][CH3:17])=[CH:12][CH:11]=1)([C:3]1[CH:8]=[CH:7][C:6]([O:9][CH2:24][CH2:25][O:26][CH2:27][CH2:28][O:29][CH3:30])=[CH:5][CH:4]=1)=[O:2]

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 74497Phenol, 4,4'-sulfinylbis-HCID 1235321-Bromo-3,6-dioxaheptane

Product 1

HCID 67608820HCID 67608820, compoundYield 85,098.102%

Reagents, catalysts & solvents 3

HCID 8037N,N,N',N'-TetramethylethylenediamineCatalystHCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Procedure

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).

Workup

  1. temperaturethe solution heated to 90° C. for 18 h
  2. temperaturecooled to r.t
  3. washwashed with water (5×500 mL)
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-355744b5a2b347f697d82a0b3fe8db40
Source dataset
uspto-grants-2014_12
Patent number
US08900792B2

Reaction notes

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