Water → HCID 58338924, compound

HRID 1888845Notes

Reaction equation

HRID 1888845 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[C:11]2=[N:12][S:13][N:14]=[C:10]2[C:9]([C:15]2[S:19][C:18]([CH2:20][OH:21])=[CH:17][CH:16]=2)=[CH:8][CH:7]=1.[CH:22]([CH:24](Cl)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=C.[H-].[Na+].O.[CH3:35]N(C=O)C>>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[C:11]2[C:10](=[N:14][S:13][N:12]=2)[C:9]([C:15]2[S:19][C:18]([CH2:20][O:21][CH2:35][C:28]3[CH:27]=[CH:26][C:25]([CH:24]=[CH2:22])=[CH:30][CH:29]=3)=[CH:17][CH:16]=2)=[CH:8][CH:7]=1

Participants

6

Reactant 5

HCID 962WaterHCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 11768772Benzene, 1-(chloromethyl)-3(or 4)-ethenyl-HCID 58338943HCID 58338943, compound

Product 1

HCID 58338924HCID 58338924, compound

Procedure

To a solution of 1.37 g (4.15 mmol) of TBT-CH2OH and 0.71 mL (5 mmol) of vinylbenzyl chloride in 60 mL DMF was added 200 mg (8.3 mmol) sodium hydride. The mixture was stirred at room temperature overnight, poured into 300 mL water and extracted with DCM (3×30 mL). The combined organic phases were consecutively washed with water and brine solution and dried over MgSO4. Purification by silica gel column chromatography with hexane:chloroform in a ratio 3:1 (v/v) gave orange powder of St-TBT (1.2 g, 64.8%).

Workup

  1. extractionextracted with DCM (3×30 mL)
  2. washThe combined organic phases were consecutively washed with water and brine solution
  3. dry with materialdried over MgSO4
  4. customPurification by silica gel column chromatography with hexane
  5. customchloroform in a ratio 3:1 (v/v) gave orange powder of St-TBT (1.2 g, 64.8%)

Sources & evidence

ORD record
ord-6a5f0189b87c470987fbde14e2ff35ea
Source dataset
uspto-grants-2013_08
Patent number
US08501889B2

Reaction notes

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