LDA

(Lithium Diisopropylamide)

General Information:

Structure:

CAS Number: 4111-54-0

Molecular Weight: 107.12 g/mol

Common Uses:

Strong base used for lithiation, typically followed by electrophilic quench (ex. formylation)

Procedure excerpt:

To a mixture of the SM (5.5 g, 18.83 mmol) and tetramethylenediamine (2.95 mL, 18.83 mmol) in anhydrous THF was added dropwise LDA (1M in heptane, 38 mL, 37.67 mmol) at -20 C . . .

[full procedure]

Strong base used for lithiation, typically followed by electrophilic quench (ex. iodination)

Procedure excerpt:

To a stirring solution of the SM (3.0 g, 20.4 mmol) in THF (15 mL) was added LDA (2.0 M in THF/heptane/ethylbenzene, 12.14 mL, 24.4 mmol) dropwise at 0 C. The mixture . . .

[full procedure]

References:

1) Patent Reference: WO2015088045, page 146, (10.3 MB)

2) Patent Reference: WO2015129926, page 152, (21.5 MB)

3) Wikipedia: Lithium diisopropylamide (link)

4) www.sigmaaldrich.com: Lithium diisopropylamide solution (link)