1-(3-(Cyclopentyloxy)-4-methoxyphenyl)ethanone → 2-Chloro-1-[3-(cyclopentyloxy)-4-methoxyphenyl]ethanone

Under a N2 flow, a solution of benzyltrimethylammonium dichloroiodate (78 g) in THF (250 ml) was added to a mixture of 1-[3-(cyclopentyloxy)-4-methoxyphenyl]ethanone (26.3 g) in THF (250 ml) while stirring. The resulting reaction mixture was stirred for 16 hours at RT. The solvent was evaporated and the residue was redissolved in diethyl ether (300 ml). The mixture was added dropwise to a 5% Na2S2O4 solution (400 ml). The aqueous layer was extracted twice with diethyl ether (2×100 ml). The combined organic layers were washed with water (2×500 ml), dried over MgSO4, filtered and the solvent evaporated. The crude oil was crystallized from hexane. The precipitate was filtered off, washed with hexane and dried, yielding 11 g of 2-chloro-1-[3-(cyclopentyloxy)-4-methoxyphenyl]ethanone. The filtrate was evaporated and the residue was crystallized from hexane. The precipitate was filtered off and dried, yielding 7.4 g (24.6%) of 2-chloro-1-[3-(cyclopentyloxy)-4-methoxyphenyl]ethanone (interm. 1).

1. customThe resulting reaction mixture
2. stirringwas stirred for 16 hours at RT
3. customThe solvent was evaporated
4. dissolutionthe residue was redissolved in diethyl ether (300 ml)
5. additionThe mixture was added dropwise to a 5% Na2S2O4 solution (400 ml)
6. extractionThe aqueous layer was extracted twice with diethyl ether (2×100 ml)
7. washThe combined organic layers were washed with water (2×500 ml)
8. dry with materialdried over MgSO4
9. filtrationfiltered
10. customthe solvent evaporated
11. customThe crude oil was crystallized from hexane
12. filtrationThe precipitate was filtered off
13. washwashed with hexane
14. customdried

ORD record

ord-ae5ffb4837bb47228741fd95e212956f

Source dataset

uspto-grants-1999_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05869515