Water → 5-[2-(3-Chloropropyloxy)ethyl]benzo[b]thiophene

HRID 1007929Notes

Reaction equation

HRID 1007929 reaction equation
[OH-].[Na+].[S:3]1[CH:7]=[CH:6][C:5]2[CH:8]=[C:9]([CH2:12][CH2:13][OH:14])[CH:10]=[CH:11][C:4]1=2.Br[CH2:16][CH2:17][CH2:18][Cl:19].O>C1(C)C=CC=CC=1.S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC>[Cl:19][CH2:18][CH2:17][CH2:16][O:14][CH2:13][CH2:12][C:9]1[CH:10]=[CH:11][C:4]2[S:3][CH:7]=[CH:6][C:5]=2[CH:8]=1

Participants

7

Reactant 4

HCID 962WaterHCID 80061-Bromo-3-chloropropaneHCID 14798Sodium HydroxideHCID 119833712-(1-Benzothiophen-5-yl)ethan-1-ol

Product 1

HCID 219900695-[2-(3-Chloropropyloxy)ethyl]benzo[b]thiophene

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 1140TolueneSolvent2×

Procedure

In a mixture of 4 mL of toluene and 8 mL of 50% (W/V) aqueous solution of sodium hydroxide is suspended 2.0 g of 2-benzo[b]thiophen-5-yl-1-ethanol, to which are added 4.4 mL of 1-bromo-3-chloropropane and 0.11 g of tetra-n-butylammonium hydrogen sulfate. The mixture is heated under reflux for 2 hours. The reaction mixture is introduced into a mixture of water and toluene, and the organic layer is separated. The organic layer is washed with water and dried over anhydrous magnesium sulfate, the solvent is distilled off under reduced pressure, and the residue is purified by column chromatography (eluent: n-hexane:ethyl acetate=10:1 to 5:1) to obtain 1.85 g of 5-[2-(3-chloropropyloxy)ethyl]benzo[b]thiophene as an oily product.

Workup

  1. temperatureThe mixture is heated
  2. temperatureunder reflux for 2 hours
  3. customthe organic layer is separated
  4. washThe organic layer is washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationthe solvent is distilled off under reduced pressure
  7. customthe residue is purified by column chromatography (eluent: n-hexane:ethyl acetate=10:1 to 5:1)

Sources & evidence

ORD record
ord-7a391cc071fd4e11a94efc3e71732528
Source dataset
uspto-grants-2004_09
Patent number
US06797726B1

Reaction notes

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