4-Toluenesulfonyl chloride → glycidyl N-tosyl-4-indolyl ether

HRID 269974Notes

Reaction equation

HRID 269974 reaction equation
[NH:1]1[C:9]2[C:4](=[C:5]([O:10][CH2:11][CH:12]3[O:14][CH2:13]3)[CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[H-].[Na+].[S:17](Cl)([C:20]1[CH:26]=[CH:25][C:23]([CH3:24])=[CH:22][CH:21]=1)(=[O:19])=[O:18]>C1COCC1.O>[S:17]([N:1]1[C:9]2[C:4](=[C:5]([O:10][CH2:11][CH:12]3[O:14][CH2:13]3)[CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1)([C:20]1[CH:26]=[CH:25][C:23]([CH3:24])=[CH:22][CH:21]=1)(=[O:19])=[O:18]

Participants

6

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 24758Sodium hydrideHCID 6050154-(oxiran-2-ylmethoxy)-1H-indole2×

Product 1

HCID 13938676glycidyl N-tosyl-4-indolyl etherYield 82.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of glycidyl 4-indolyl ether (compound 1a) (1.0 g, 5.3 mmol) in THF (5 mL) was cooled to 0° C., and sodium hydride in mineral oil (60%, 0.42 g, 10.6 mmol) and tosyl chloride (1.2 g, 6.3 mmol) were added. After being stirred at this temperature for 1 h, the reaction mixture was allowed to warm to room temperature and stirred for 2 hours. The reaction mixture was diluted with water and extracted with CHCl3 (3.50 mL). The combined organic layers were dried with Na2SO4 and concentrated. The residue was purified by column chromatography on silica gel with benzene/acetone mixtures to give the glycidyl N-tosyl-4-indolyl ether (compound 1b) (1.5 g, 82%) as a white solid. See FIG. 18.

Workup

  1. stirringstirred for 2 hours
  2. extractionextracted with CHCl3 (3.50 mL)
  3. dry with materialThe combined organic layers were dried with Na2SO4
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography on silica gel with benzene/acetone

Sources & evidence

ORD record
ord-0fc75a0f1e3447f29c4c8ef0f2fcdfb3
Source dataset
uspto-grants-2008_11
Patent number
US07449480B2

Reaction notes

Loading…