Ammonium Chloride → 1-(3-Cyclopentyloxy-4-methoxyphenyl)-2-(2,6-dichlorophenyl)ethanol

Temperatur

-70 °C

A solution of butyl lithium in hexane (5.1 mL; 2.5 M) is treated with a solution of 3-cyclopentyloxy-4-methoxyphenyl bromide (3.45 g) in dry tetrahydrofuran (30 mL) at −70° C. and the solution is then stirred at −70° C. for 1 hour. It is then treated dropwise with 2,6-dichlorophenylacetaldehyde (2.4 g), while keeping the temperature below −60° C. When the addition is complete the temperature is allowed to rise to room temperature and the solution is stirred for a further 2 hours. The reaction mixture is treated with aqueous ammonium chloride solution (50 mL) and the solution is extracted with diethyl ether (2×200 mL). The combined extracts are dried and concentrated, to give a yellow oil, which is subjected to flash chromatography, eluting with a mixture of diethyl ether and pentane (1:8 v/v), to give 1-(3-cyclopentyloxy-4-methoxyphenyl)-2-(2,6-dichlorophenyl)ethanol (1.6 g), in the form of a white solid, m.p. 87-89° C.

1. customthe temperature below −60° C
2. additionWhen the addition
3. customto rise to room temperature
4. stirringthe solution is stirred for a further 2 hours
5. extractionthe solution is extracted with diethyl ether (2×200 mL)
6. customThe combined extracts are dried
7. concentrationconcentrated
8. customto give a yellow oil, which
9. washeluting with a mixture of diethyl ether and pentane (1:8 v/v)

ORD-Eintrag

ord-338916d34a664074a754ccd37290a004

Quelldatensatz

uspto-grants-2001_07

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US06255326B1