Water → (E)-2-(2-(2-(2-tosyloxyethoxy)ethoxy)ethoxy)-5-(4-dimethylaminostyryl)pyridine

HRID 77246Notes

Reaction equation

HRID 77246 reaction equation
[S:1](Cl)([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2].[OH:12][CH2:13][CH2:14][O:15][CH2:16][CH2:17][O:18][CH2:19][CH2:20][O:21][C:22]1[CH:27]=[CH:26][C:25](/[CH:28]=[CH:29]/[C:30]2[CH:35]=[CH:34][C:33]([N:36]([CH3:38])[CH3:37])=[CH:32][CH:31]=2)=[CH:24][N:23]=1.O>N1C=CC=CC=1>[S:1]([O:12][CH2:13][CH2:14][O:15][CH2:16][CH2:17][O:18][CH2:19][CH2:20][O:21][C:22]1[CH:27]=[CH:26][C:25](/[CH:28]=[CH:29]/[C:30]2[CH:35]=[CH:34][C:33]([N:36]([CH3:38])[CH3:37])=[CH:32][CH:31]=2)=[CH:24][N:23]=1)([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2]

Participants

5

Reactant 3

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 67384227(E)-2-(2-(2-(2-Hydroxyethoxy)ethoxy)ethoxy)-5-(4-dimethylaminostyryl)pyridine

Product 1

HCID 86618273(E)-2-(2-(2-(2-tosyloxyethoxy)ethoxy)ethoxy)-5-(4-dimethylaminostyryl)pyridineYield 41%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
0 °C

Procedure

Tosyl chloride (52 mg, 0.27 mmol) was added to a solution of compound 9 (43 mg, 0.116 mmol) in pyridine (5.0 ml) at 0° C. The reaction mixture was stirred at 0° C. for 1 h and then warmed up to room temperature and stirred for 3 h. Water was added and reaction mixture was extracted with ethyl acetate. Organic layer was separated, washed with brine, dried over sodium sulfate and evaporated. The residue was purified by PTLC (4% MeOH in DCM as developing solvent) to give product 10 (25 mg, Yield: 41%): 1H NMR (200 MHz, CDCl3): δ.8.14 (1H, d, J=2.0 Hz), 7.76 (3H, m), 7.39 (2H, d, J=8.8 Hz), 7.32 (2H, d, J=8.0 Hz), 6.87 (2H, m), 6.75 (3H, m), 4.46 (2H, t, J=4.6 Hz), 4.16 (2H, t, J=4.8 Hz), 3.81 (2H, t, J=4.8 Hz), 3.66 (6H, m), 2.99 (6H, s), 2.43 (3H, s), HRMS (EI) m/z calcd. for [C28H34N2O6S]+ 526.2138.

Workup

  1. temperaturewarmed up to room temperature
  2. stirringstirred for 3 h
  3. customreaction mixture
  4. extractionwas extracted with ethyl acetate
  5. customOrganic layer was separated
  6. washwashed with brine
  7. dry with materialdried over sodium sulfate
  8. customevaporated
  9. customThe residue was purified by PTLC (4% MeOH in DCM as developing solvent)

Sources & evidence

ORD record
ord-3a6fc172e2fe4ce6a76ca44ea4d1d2b1
Source dataset
uspto-grants-2014_09
Patent number
US08840866B2

Reaction notes

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