Hexane → 6-Decyl-3-methylthio-2-methoxynaphthalene

Participants

Reaction Steps

A hexane solution of 1.57 Mn—BuLi (28 ml, 44 mmol) was added to a THF (100 ml) solution of 6-n-decyl-2-methoxynaphthalene (compound (3)-64) (12 g, 40 mmol) at −78° C., and the solution was stirred at room temperature for 1 hour. Dimethyl disulfide (4.4 ml, 48 mmol) was added to the solution at −78° C., and the solution was stirred at room temperature for 18 hours. The reaction solution was added to a saturated ammonium chloride aqueous solution (50 ml), and extracted with ether (30 ml×3). The extracted solutions obtained by repeating the extraction 3 times were collected, washed with a saturated saline water (30 ml×3), and dried with MgSO4. The dried product was condensed with an evaporator to obtain 6-n-decyl-3-methylthio-2-methoxynaphthalene (compound (4)-64) (15.2 g, quantitative) as a yellow oil. The compound can be used in the subsequent reaction without performing further refining.

Provenance & Evidence