Water → 5-allyloxy-1-benzenesulfonyl-1H-indole

HRID 2243167Notes

Reaction equation

HRID 2243167 reaction equation
[H-].[Na+].[CH2:3]([O:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[NH:12][CH:11]=[CH:10]2)[CH:4]=[CH2:5].[C:16]1([S:22](Cl)(=[O:24])=[O:23])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.O>C1COCC1>[CH2:3]([O:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[N:12]([S:22]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)(=[O:24])=[O:23])[CH:11]=[CH:10]2)[CH:4]=[CH2:5]

Participants

6

Reactant 4

HCID 962WaterHCID 7369Benzenesulfonyl chlorideHCID 24758Sodium hydrideHCID 142392305-(prop-2-en-1-yloxy)-1H-indole

Product 1

HCID 685493765-allyloxy-1-benzenesulfonyl-1H-indoleYield 48.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a slurry of 0.45 g (9.4 mmol) sodium hydride (50% dispersion in mineral oil) in 40 mL anhydrous THF was added 1.90 g 5-allyloxyindole. The slurry was stirred at room temperature for 15 min upon which time 1.14 mL (9 mmol) benzene sulfonyl chloride was added dropwise. The reaction was stirred at room temperature over three nights and then poured into water and extracted with ethyl acetate. The organic extracts were dried over MgSO4 and concentrated. The product solidified upon concentration and the crude material was triturated with diethyl ether to afford 1.36 g of 5-allyloxy-1-benzenesulfonyl-1H-indole as a light brown solid.

Workup

  1. additionwas added dropwise
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic extracts were dried over MgSO4
  4. concentrationconcentrated
  5. concentrationThe product solidified upon concentration
  6. customthe crude material was triturated with diethyl ether

Sources & evidence

ORD record
ord-a5c1120043394832be0509a5cbce0f84
Source dataset
uspto-grants-2010_03
Patent number
US07674818B2

Reaction notes

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