Diisopropylamine → Lithium diisopropylamide

HRID 1196920Notes

Reaction equation

HRID 1196920 reaction equation
C([Li:5])CCC.[CH:6]([NH:9][CH:10]([CH3:12])[CH3:11])([CH3:8])[CH3:7].[CH2:13]([C:15]1[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=1)[CH3:14].Cl[CH2:22][C:23]([C:25]1[CH:30]=[CH:29][C:28]([F:31])=[CH:27][C:26]=1[F:32])=[O:24]>CCCCCC.O1CCCC1>[CH:6]([N-:9][CH:10]([CH3:12])[CH3:11])([CH3:8])[CH3:7].[Li+:5].[F:32][C:26]1[CH:27]=[C:28]([F:31])[CH:29]=[CH:30][C:25]=1[C:23]1([CH:13]([C:15]2[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=2)[CH3:14])[CH2:22][O:24]1

Participants

8

Reactant 4

HCID 7912DiisopropylamineHCID 108224-EthylpyridineHCID 5880832-Chloro-1-(2,4-difluorophenyl)ethanoneHCID 178418339Butyllithium

Product 2

HCID 2724682Lithium diisopropylamideHCID 189565302-(2,4-Difluorophenyl)-2-(1-[pyridin-4-yl]ethyl)oxirane

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

Lithium diisopropylamide was prepared by addition of n-butyllithium (19.7 ml of a 1.6M solution in hexane) to a solution of diisopropylamine (3.18 g) in dry tetrahydrofuran (50 ml), and the resulting solution was treated successively with 4-ethylpyridine (3.37 g) and a solution of 2-chloro-2',4'-difluoroacetophenone (5.00 g) in dry tetrahydrofuran (50 ml) according to the method of Example 1(i). Work-up of the reaction mixture as before afforded the title compound (1.05 g) as a yellow oil which was used directly in the next stage.

Sources & evidence

ORD record
ord-3fff3c09df244622a74c8f0a275e1f53
Source dataset
uspto-grants-1992_05
Patent number
US05116844

Reaction notes

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