Sodium Hydroxide → HCID 131718283, compound

Participants

Reaction Steps

Methyl (1S, 4aS, 7R, 7aR)-1-[1-(ethoxy)ethoxy]-1, 4a, 5, 6, 7, 7a-hexahydro-7-methylcyclopenta[c]pyran-4-carboxylate (3.00 g, 0.011 mol) obtained in Example 24 was dissolved in 70 ml of anhydrous tetrahydrofuran, and while the reaction mixture was being cooled with ice and stirred, 14.8 ml of diisobutylaluminum hydride (1.5M toluene solution) was added dropwise. The reaction mixture was stirred at the same temperature for 2 hours, 1.6 ml of acetone was added dropwise and the reaction mixture was again stirred for 20 minutes. Furthermore, 2 ml of 3% sodium hydroxide solution was added dropwise and the reaction mixture was stirred for 1 hour. After magnesium sulfate was added, the reaction mixture was further stirred for 20 minutes, unnecessary matters were filtered by a celite and the solvent was distilled off under a reduced pressure A colorless oily substance was thus obtained, i.e., (1S, 4aS, 7R, 7aR)-1-[1-(ethoxy)ethoxy]-1, 4a, 5, 6, 7, 7a-hexahydro-4-(hydroxymethyl)-7-methylcyclopenta[c]pyran (2.18 g, yield=81.5%). This (1S, 4aS, 7R, 7aR)-1-[1-(ethoxy)ethoxy]-1, 4a, 5, 6, 7, 7a-hexahydro-4(hydroxymethyl)- 7-methylcyclopenta[c]pyran had the following physicochemical properties:

Provenance & Evidence