m,alpha-Dichlorotoluene → HCID 70240212, compound

Participants

Reaction Steps

2-Ethyl-5-methoxy-1H-indole-3-acetic acid ethyl ester (1.82 g, 7.4 mmol) was added to 296 mg (7.4 mmol) of NaH/mineral oil (previously washed with hexane), the mixture stirred for 0.5 hours and 0.93 mL (7.4 mmol) of 3-chlorobenzyl chloride added. After 21 hours, water was added and the mixture extracted with ethyl acetate. The ethyl acetate was washed with brine, dried (MgSO4) and concentrated at reduced pressure. The residue was chromatographed on silica gel eluting with 20% EtOAc/hexane to give 2.13 g (75% yield) of 1-[(3-chlorophenyl)methyl]-2-ethyl-5-methoxy-1H-indole-3-acetic acid ethyl ester as an oil.

Provenance & Evidence