Tetrahydrofuran → Diisopropylamine

HRID 6284Notes

Reaction equation

[CH:1]([N-:4][CH:5]([CH3:7])[CH3:6])([CH3:3])[CH3:2].[Li+:8].O1[CH2:13][CH2:12][CH2:11][CH2:10]1>>[CH2:10]([Li:8])[CH2:11][CH2:12][CH3:13].[CH:1]([NH:4][CH:5]([CH3:7])[CH3:6])([CH3:3])[CH3:2]

Participants

Reactant 2

HCID 8028Tetrahydrofuran

HCID 2724682Lithium diisopropylamide

Product 2

HCID 7912Diisopropylamine

HCID 178418339Butyllithium

Procedure

A mixture of 10 mmole of lithium diisopropylamide (LDA), formed from n-butyllithium and diisopropylamine, in 10 mL of tetrahydrofuran was cooled to -78° C. Then 2 g of α-isopropyl-3,4-dimethoxybenzyl nitrile was added to the mixture. The reaction mixture was stirred at -78° C. for 20 minutes, 0.78 mL of epibromohydrin was added and stirring was continued for an additional two hours. The reaction mixture was then added to aqueous hydrochloric acid, the aqueous solution was extracted with ether and the ether extracts were combined. The combined extracts were dried over magnesium sulfate, filtered and the organic solvent was removed from the filtrate to provide 2.66 g of an oil which was used immediately in Step (b), below.

Sources & evidence

ORD record: ord-4b6f82fdc15f49e3b6f995f7f804f355
Source dataset: uspto-grants-1993_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05247119

Reaction notes

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