Methyl Ethyl Ketone → Lithium diisopropylamide

HRID 2116645Notes

Reaction equation

HRID 2116645 reaction equation
[Li+:1].[CH3:2][CH:3]([N-:5][CH:6]([CH3:8])[CH3:7])[CH3:4].[SH:9][C:10]1[S:11][CH:12]=[CH:13][N:14]=1.[CH3:15][C:16](=[O:19])[CH2:17][CH3:18]>C1COCC1.CCOCC>[Li+:1].[CH3:2][CH:3]([N-:5][CH:6]([CH3:8])[CH3:7])[CH3:4].[SH:9][C:10]1[S:11][C:12]([C:16]([OH:19])([CH2:17][CH3:18])[CH3:15])=[CH:13][N:14]=1

Participants

7

Reactant 3

HCID 6569Methyl Ethyl KetoneHCID 2724682Lithium diisopropylamideHCID 178527881HCID 178527881, compound

Product 2

HCID 2724682Lithium diisopropylamideHCID 178450294HCID 178450294, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

A solution of LDA (59 mmol) in THF was prepared at −10° C. and cooled to −78° C. To the LDA was added a solution of 2-mercaptothiazole (3.00 g, 25.6 mmol) in 5 mL of THF. After 15-20 min of stirring a solution of 2-butanone (2.23 mL, 38.4 mmol) was added, and the reaction mixture was stirred at −78° C. for 2 h. The reaction mixture was diluted with ether and washed successively with aq. 2N HCl, H2O and brine, dried over MgSO4, filtered and concentrated. The crude product was washed with Et2O to give the title compound.

Workup

  1. additionwas added
  2. washwashed successively with aq. 2N HCl, H2O and brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. washThe crude product was washed with Et2O

Sources & evidence

ORD record
ord-d0c2aabf89524d03b7903f7070e2450c
Source dataset
uspto-grants-2008_10
Patent number
US07439260B2

Reaction notes

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