Hydrochloric Acid → 5-(4-Chlorobenzyl)-8-hydroxy-4-(2-hydroxyethyl)-2-methyl-3,5-dihydro-2H-thiopyrano[4,3,2-cd]indole

Participants

Reaction Conditions

Reaction Steps

To a suspension of 97% NaH (120 mg, 4.88 mmol) in DMF (10 mL) and DMPU (1 mL) cooled to 0° C., there was added 2-methyl-2-propanethiol (550 mg, 6.10 mmol) and the resulting mixture was stirred at 0° C. for one hour. To this clear solution there was added a solution of product from Step 4 (490 mg, 1.22 mmol) in DMF (4 mL). The mixture was heated at 140° C. for 19 hours, cooled, diluted with H2O, acidified with 1N HCl and extracted 3× with Et2O. These extracts were washed 2× with brine, dried, and evaporated. The residue was chromatographed on silica gel, eluting with a 1:1 mixture of EtOAc and hexane, to afford the title product as a thick oil.

Provenance & Evidence