Ethyl trifluoroacetate → Lithium diisopropylamide

HRID 2116640Notes

Reaction equation

HRID 2116640 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.[F:15][C:16]([F:23])([F:22])[C:17](OCC)=[O:18]>C1COCC1>[Li+:1].[CH3:2][CH:3]([N-:5][CH:6]([CH3:8])[CH3:7])[CH3:4].[F:15][C:16]([F:23])([F:22])[C:17]([C:12]1[S:11][C:10]([SH:9])=[N:14][CH:13]=1)=[O:18]

Participants

6

Reactant 3

HCID 9794Ethyl trifluoroacetateHCID 2724682Lithium diisopropylamideHCID 178527881HCID 178527881, compound

Product 2

HCID 2724682Lithium diisopropylamideHCID 178519847HCID 178519847, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
-78 °C

Procedure

A solution of LDA (95.4 mmol) in THF was prepared at −10° C. and cooled to −78° C. To the LDA was added a solution of 2-mercaptothiazole (10.00 g, 85.3 mmol) in 25 mL of THF. After 15-30 min of stirring, ethyl trifluoroacetate (13.2 mL, 110.9 mmol) in 15 mL of THF was added. The solution was brought to −10° C. and quenched with NH4Cl followed by HCl (10%) and diluted with EtOAc. The layers were separated and the aqueous phase was extracted with EtOAc. The combined organic layers were dried over anhydrous MgSO4. The solvent was evaporated and the residue chromatographed on silica gel (toluene/acetone; 8:2 with 1% methanol) to give the title compound.

Workup

  1. customwas brought to −10° C.
  2. customquenched with NH4Cl
  3. additiondiluted with EtOAc
  4. customThe layers were separated
  5. extractionthe aqueous phase was extracted with EtOAc
  6. dry with materialThe combined organic layers were dried over anhydrous MgSO4
  7. customThe solvent was evaporated
  8. customthe residue chromatographed on silica gel (toluene/acetone; 8:2 with 1% methanol)

Sources & evidence

ORD record
ord-ade95a65338549ceb58fcdfd9330f736
Source dataset
uspto-grants-2008_10
Patent number
US07439260B2

Reaction notes

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