Tetrahydrofuran → Diisopropylamine

HRID 2253561Notes

Reaction equation

HRID 2253561 reaction equation
[CH:1]([N-:4][CH:5]([CH3:7])[CH3:6])([CH3:3])[CH3:2].[Li+:8].[CH2:9]1[CH2:13]O[CH2:11][CH2:10]1>CCCCCC>[CH:1]([NH:4][CH:5]([CH3:7])[CH3:6])([CH3:3])[CH3:2].[CH2:11]([Li:8])[CH2:10][CH2:9][CH3:13]

Participants

5

Reactant 2

HCID 8028Tetrahydrofuran2×HCID 2724682Lithium diisopropylamide

Product 2

HCID 7912DiisopropylamineHCID 178418339Butyllithium

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

A solution of the ketone 26a (60 mg) in THF (0.5 ml) is added at -78° C. to a solution of lithium diisopropylamide, obtained from diisopropylamine (0.024 ml) and n-butyllithium (0.084 ml of a 2 molar solution in hexane) in THF (0.5 ml). The temperature is brought back to -40° C. for 10 minutes. A solution of phenylselenyl bromide (40 mg) in THF (0.5 ml) is then added dropwise at -78° C. Water and ether are added. The organic phase is washed with water, bicarbonate and brine, and dried. After concentration under vacuum, the residue is purified on silica gel (ether/hexane, 1:9), to give 40 mg of selenide 32a (50% yield).

Sources & evidence

ORD record
ord-9b307ffe068049f3849987f0438a5653
Source dataset
uspto-grants-1993_08
Patent number
US05232836

Reaction notes

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