[qw098]

Hi guys,

I got a question regarding the synthesis of tamoxifen from some reagents. I was wondering if my thought-process was correct.
Here is a picture of the question:

 Here are my steps:

1)PPh3-CH2Ch2Ch3
2)NaBH4, CH3OH
3)PCC
4)Benzene-MgBr

I applied all these reagents in sequential order to the compound to the left of tamoxifen below in order to get tamoxifen.

 I would appreciate it if you guys can let me know if this is right as it took me a good 30 minutes to think of this possibility! I couldn't hit supper well without thinking about this problem! haha

Thanks!

[Honclbrif]

I'd take another look at that first step. Is it going to leave you with anything that NaBH₄ can chew on?

[qw098]

Won't it leave me with a double bond?

Instead of NaBH4 I meant to say BH3 in THF then H2O2 in NaOH so I get an alcohol in the less substituted position?

Would that be that correct approach?

So:

1)PPh3-CH2Ch2Ch3
2)BH3, THF ; H2O2, NaOH
3)PCC
4)Benzene-MgBr

[Honclbrif]

That sounds better