1-(Chloromethyl)-4-(methylthio)benzene → 2-Methyl-3-(4-methylthiobenzyl)-1-indanone

To a cooled solution (−70° C.) of LDA (1 M) in THF (37 mL) was added dropwise a solution of 2-methyl-1-indanone (J.A.C.S. Vol. 98, 8119-8124 (1976)) (2.5 g, 17 mmol) in THF (20 mL). The resulting dark red solution was stirred at room temperature for 3 hours, then cooled to −20° C. and a solution for 4-methylthiobenzyl chloride (3.1 g, 18 mmol) in THF (15 mL) was added slowly. The addition completed, the reaction mixture was stirred at −20° C. for 30 minutes before being quenched with 3N aqueous HCl (50 mL) and brine (50 mL). The product was extracted with ether, dried over MgSO4 and evaporated to dryness. The oily residue was chromatographed on silica gel eluting with a 1:5 mixture of ethyl acetate-hexane to afford the pure title compound as an oil.

1. temperaturecooled to −20° C.
2. additionThe addition
3. stirringthe reaction mixture was stirred at −20° C. for 30 minutes
4. custombefore being quenched with 3N aqueous HCl (50 mL) and brine (50 mL)
5. extractionThe product was extracted with ether
6. dry with materialdried over MgSO4
7. customevaporated to dryness
8. customThe oily residue was chromatographed on silica gel eluting with a 1:5 mixture of ethyl acetate-hexane

ORD record

ord-6e463c8082fe4fbbbdd06b9eff4ef69d

Source dataset

uspto-grants-2001_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06300346B1