Water → HCID 58338924, compound

HRID 881782Notes

Reaction equation

HRID 881782 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-1730ea62d871452d9193779379430824
Source dataset
uspto-grants-2015_03
Patent number
US08993697B2

Reaction notes

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