Benzenesulfonyl chloride → benzenesulphonic acid 2-(1-benzenesulphonyl-5-methoxy-1H-indol-3-yl)ethyl ester

HRID 635381Notes

Reaction equation

HRID 635381 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]2[NH:9][CH:10]=[C:11]([CH2:12][CH2:13][OH:14])[C:5]=2[CH:4]=1.[C:15]1([S:21](Cl)(=[O:23])=[O:22])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.[OH-].[Na+].ClCCl>[C:15]1([S:21]([N:9]2[C:6]3[C:5](=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=3)[C:11]([CH2:12][CH2:13][OH:14])=[CH:10]2)(=[O:23])=[O:22])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[C:15]1([S:21]([N:9]2[C:6]3[C:5](=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=3)[C:11]([CH2:12][CH2:13][O:14][S:21]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)(=[O:23])=[O:22])=[CH:10]2)(=[O:23])=[O:22])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

7

Reactant 2

HCID 7369Benzenesulfonyl chloride2×HCID 128355-Methoxytryptophol

Product 2

HCID 11762460benzenesulphonic acid 2-(1-benzenesulphonyl-5-methoxy-1H-indol-3-yl)ethyl esterYield 52%HCID 212585582-(1-Benzenesulphonyl-5-methoxy-1h-indol-3-yl)ethanolYield 37%

Reagents, catalysts & solvents 3

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 6344DichloromethaneSolventHCID 14798Sodium HydroxideSolvent

Procedure

To a stirred two-phase mixture of 5-methoxytryptophol (0.150 g, 0.785 mmol) and tetrabutylammonium hydrogen sulphate (27 mg, 0.0785 mmol) in 50% aqueous NaOH (3 ml) and dichloromethane (30 ml) was added benzenesulphonyl chloride (0.25 ml, 1.96 mmol) dropwise over 5 min. The mixture was stirred for 20 min, more benzenesulphonyl chloride 0.10 ml, 0.784 mmol) was added dropwise, and the mixture was stirred for a further hour. The organic layer was washed with brine, dried (Na2SO4) and evaporated in vacuo. The residue was purified by flash chromatography (silica gel, 50-100% EtOAc/hexane) to afford 0.095 g (37%) of 2-(1-benzenesulphonyl-5-methoxy-1H-indol-3-yl)ethanol and 0.191 g (52%) of the title compound; δH (360 MHz, d6-DMSO) 2.98 (2H, t, J 6.1 Hz), 3.71 (3H, s), 4.30 (2H, t, J=6.2 Hz), 6.92 (1H, dd, J=8.9, 2.5 Hz), 6.95 (1H, d, J=2.2 Hz), 7.47 (2H, t, J=7.8 Hz), 7.53-7.59 (3H, m), 7.63-7.67 (4H, m), 7.77 (1H, d, J=8.9 Hz), 7.89 (2H, m); m/z (ES+) 510 (M+K)+, 494 (M+Na)+, 489 (M+NH4)+, 472 (M+H)+.

Workup

  1. stirringthe mixture was stirred for a further hour
  2. washThe organic layer was washed with brine
  3. dry with materialdried (Na2SO4)
  4. customevaporated in vacuo
  5. customThe residue was purified by flash chromatography (silica gel, 50-100% EtOAc/hexane)

Sources & evidence

ORD record
ord-f17e41db28c44fc2b4ce637d3756d6eb
Source dataset
uspto-grants-2001_02
Patent number
US06187805B1

Reaction notes

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