[Marycat16]

I'm trying to reduce the methyl ester of a diterpene, but a I have not success.

NaBH4/I2And I 'm using this system. Someone has used ?

I have a flask ester solution in THF ,

I have another flask a solution of NaBH4 in THF

And I have another flask a solution of iodine in THF.

Then I added the ester solution to the solution of NaBH4 , after 10 minutes, add the iodine solution .

The article mentions that owe iodine added in 30 minutes but it added in 10 minutes , it affects ?

My tetrahydrofuran is impure also , I put on a TLC plate eluting off a compound .

Could anyone help me?

[kriggy]

1) get pure THF
2) add the iodine in 30 minutes not 10
3) see what happens

anyway, what do you mean by not succes? side reactions? no reduction at all? partial reduction?

[Dan]

I'm trying to reduce the methyl ester of a diterpene, but a I have not success.

NaBH4/I2And I 'm using this system. Someone has used ?

I have a flask ester solution in THF ,

I have another flask a solution of NaBH4 in THF

And I have another flask a solution of iodine in THF.

Then I added the ester solution to the solution of NaBH4 , after 10 minutes, add the iodine solution .

The article mentions that owe iodine added in 30 minutes but it added in 10 minutes , it affects ?

My tetrahydrofuran is impure also , I put on a TLC plate eluting off a compound .

Could anyone help me?

Yeah, I've used this a couple of times. What you are doing here is generating borane (and NaI) from NaBH₄ and I₂. When I did it, I did the order of addition differently: I added I₂ THF solution dropwise to a suspension of NaBH₄ in THF at 0 ^oC. Once the solution decolourised, I added my ester.

You should use anhydrous THF and an inert atmosphere.

[TheUnassuming]

Dan- Random side question.  What is the benefit of using this system vs standard BH3-THF?

[Dan]

Dan- Random side question.  What is the benefit of using this system vs standard BH3-THF?

None as far as I'm aware. The only times I used it was when either the bottle BH₃ had run out or had obviously degraded.