Lithium diisopropylamide → Diisopropylamine

HRID 1604829Notes

Reaction equation

HRID 1604829 reaction equation
[CH3:1][CH:2](P(O)(O)=O)/[C:3](/[CH3:9])=C(\C)/C([O-])=O.[CH:14]([N-:17][CH:18]([CH3:20])[CH3:19])([CH3:16])[CH3:15].[Li+:21]>C1COCC1>[CH:14]([NH:17][CH:18]([CH3:20])[CH3:19])([CH3:16])[CH3:15].[CH2:1]([Li:21])[CH2:2][CH2:3][CH3:9]

Participants

5

Reactant 2

HCID 2724682Lithium diisopropylamideHCID 71651211Trimethyl4-phosphonocrotonate

Product 2

HCID 7912DiisopropylamineHCID 178418339Butyllithium

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Alternatively, the solution of trimethyl-4-phosphonocrotonate in THF is deprotonated at -78° C. with a solution of lithium diisopropylamide (LDA), obtained from diisopropylamine and n-butyllithium, in THF, and the obtained anion reacted at -78° C. with a solution of an aldehyde IX in THF.

Sources & evidence

ORD record
ord-5ea4a9ab413a4bdcbc2a3c22dafa88ac
Source dataset
uspto-grants-1999_11
Patent number
US05994569

Reaction notes

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