Dimethyl Sulfoxide → 4-(3-chloropropoxy)-1H-indole

A mixture of 4-hydroxyindole (0.100 g, 0.75 mmol, 1.0 eq), powdered potassium hydroxide (0.042 g, 0.75 mmol, 1.0 eq), and DMSO (3 mL) was stirred at room temperature for 1 hour before 1-bromo-3-chloropropane (0.118 g, 0.75 mmol, 1.0 eq) was added. The above mixture was then stirred at room temperature for another 0.5 hour and then 15 mL of water was added to it. The resultant mixture was extracted with ethyl acetate (2×30 mL). The organic layer was collected, combined, washed with water (6×25 mL) and brine (2×20 mL), and dried over anhydrous Na2SO4. The solvent was removed in vacuo and the residue was purified by flash chromatography over silica gel using hexane/ethyl acetate (95/5) as an eluant to afford 4-(3-chloropropoxy)-1H-indole (0.130 g, yield: 83%).

1. additionwas added
2. extractionThe resultant mixture was extracted with ethyl acetate (2×30 mL)
3. customThe organic layer was collected
4. washwashed with water (6×25 mL) and brine (2×20 mL)
5. dry with materialdried over anhydrous Na2SO4
6. customThe solvent was removed in vacuo
7. customthe residue was purified by flash chromatography over silica gel

ORD record

ord-78f085902122462bb71a1fba8ca88f4d

Source dataset

uspto-grants-2008_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07449478B2