we can use from LiAlH4

I don't have a reference for selective carbonyl reductions in the presence of olefins but you should be able to do it in a two step process; first selective reduction of the carbonyl to the alcohol with NaBH4 or LiAlH4. Followed by tosylation of the alcohol and reduction of the tosylate with LiAlH4 without the reduction of the alkene.

May be it will reduct throug sodium amalgum.iam not sure. Check once

This reference could be useful for you, where keto functional group of chalcone has been reduced to –CH2 selectively by (MeO)3SiH, ZnCl2 (10 min, rt) without affecting double bond.

Reference: Phosphorus, Sulfur and Silicon and the Related Elements, 2011, 186(8), 1621-1625

one method you can try is Wolf Kishner reduction, another would be convert the keto to tosyl hydrazone and reduction of tosyl hydrazone with sodium cyano borohydride, there may be chance of isomerisation of doublebond .

wt abt Clemmenson reduction? will it help? i don't knw its practical effects, bt studied that its a selective reducing agent fr carbonyl group to CH2

Clemenson reduction would reduce the double bond as well !!!

Try conversion of the ketone into thioketone using 1,2-ethanedithiol and reduce with Ra-Ni.

AlCl3+LiAlH4 may work, otherwise you have to had a multi-steps process as Oliver Gleeson said.

See synthesis of drugs in www.drugsyn.org

Make hydroxy by normal reduction and later convert to chloro by thionyl chloride and then further reduction to CH2 group.

Regards

Rajesh

Thank you all for the support.

Use LiALH4 reduction in dry ether to reduce carbonyl group

uuse peterson olefication........... DB will not affect..

wolf & clemensens will reduce whole corbonyl grp to CH2.........simple ......... see above reaction

Please try to go for clemensens reduction, it should definitely work coz clemensens and wolf-kishner reactions is mean to reduce carbonyl to CH2... if the clemensons doent suits for ur reaction then try to react carbonyl with tosyl hydrazene and then treat it with NaBH4 in aceticacid, it will reduce carbonyl to CH2 with out affecting double bond.

you want to convert =C=O to =CH2 or =C=O to =C=CH2 ? clear it

Mr. K.. Rajesh , reduction of unsaturated carbonyl group with tosyl hydrazene and then treat it with NaBH4 in aceticacid, the position of double bond change, reaction known as "alkene walk".

youn can use clemmensons reduction amalgamated zinc and Hcl, it specfically reduces ketonic group into alkyl group

Dont use NaBH4 because it reduces only ketonic group ti secindary alcohol. prefer clemenson or wolf kishner reduction

hi dear ranvijay, what u said is right the α,β-Unsaturated carbonyl compounds are reduced with concomitant migration of the conjugated alkene. The mechanism for this "alkene walk" reaction apparently proceeds through a diazene intermediate which transfers hydride by 1,5-sigmatropic rearrangement. but in some cases where the compound is fully unsaturated one... in order to maintain its unsaturation the double bond shift may not occur... for example consider the reduction of cinnamaldehyde and 2(nitrovinyl)benzene with LiAlH4, the double bond in cinnamaldehyde can not get reduced, where unsaturation prevails in this case, like wise some times alkene walk may not occur in case of compounds with high degree of unsaturation... so i just told to give a trail...

Dear Apurba Sinhamahapatra if u think that all the above said procedures does nt work and if u need the compound with the unsaturation then convert the carbonyl to acid (-COOH) and then decarboxylate it.

Wolfkishner reaction will works good which reduces keto to CH2, try it, sure it may