Method for the preparation of 2-{2-[4-(4-chloro-1,2-diphenylbut-1-enyl)phenoxy]ethoxy}ethanol and its isomers

1. Method for the preparation of the compound (I), which is therapeutically useful as a selective estrogen receptor modulator,

wherein

a) a compound of formula (II)

R—O—CH 2 CH 2 —O—CH 2 CH 2 —R′  (II)

where R is a protecting group and R′ is halogen, —OSO 2 CH 3 or tosylate, is reacted with 4-hydroxybenzophenone to give a compound of formula (III),

b) the compound (III) is reacted with cinnamaldehyde and LiAlH 4 in a suitable solvent to give a compound of formula (IV)

c) the compound (IV) is reacted with thionyl chloride in a suitable solvent to give a compound of formula (V)

and

d) the protecting group R is removed from the compound (V) to give the compound of formula (I).

2. The method of claim 1 , wherein the protecting group R is allyl, benzyl or substituted benzyl.

3. The method of claim 1 , wherein the reaction in step a) is carried out as a phase-transfer catalysis, and the solvent in step b) is tetrahydrofuran and the solvent in step c) is toluene.

4. The method of claim 1 , wherein the removal of the protecting group in step d) is carried out i) by hydrogenation with metal catalyst in appropriate solvent or ii) by selective cleavage of a nonaromatic ether with Zn/Acyl chloride.

5. A compound of formula (IV)

wherein R is a protecting group.

6. A compound of formula (V)

wherein R is allyl, benzyl or substituted benzyl.

7. The compound of (V) claim 6 , wherein R is benzyl.

8. The method of claim 1 , wherein R′ is Cl.