Dimethylformamide → HCID 18793049, compound

HRID 850647

Reaction equation

HRID 850647 reaction equation
[Li+].CC([N-]C(C)C)C.[Br:9][C:10]1[C:14]([CH2:15][CH2:16][CH2:17][CH3:18])=[CH:13][S:12][CH:11]=1.CN([CH:22]=[O:23])C>C1COCC1>[Br:9][C:10]1[C:14]([CH2:15][CH2:16][CH2:17][CH3:18])=[CH:13][S:12][C:11]=1[CH:22]=[O:23]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 2724682Lithium diisopropylamideHCID 125026793-Bromo-4-butylthiophene

Product 1

HCID 18793049HCID 18793049, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

To a solution of freshly prepared LDA (11.40 mmol) in THF (7 mL) at -78° C. was added slowly 3-bromo-4-butylthiophene of Example l(a) (2.50 g, 11.40 mmol) in THF (10 mL). After stirring for 15 min, DMF (0.94 mL, 12.10 mmol) in THF (2 mL) was dropwise added. The resulting mixture was stirred for 1 h at -78° C. and then allowed to warm to room temperature. The reaction was quenched with water and extracted with EtOAc (2×50 mL). The combined organic extracts were washed with H2O, brine and dried (MgSO4). After removing the solvent under reduced pressure, column chromatography (silica gel, EtOAc/Hexane, 20:80) of the residue afforded the title compound as an oil (1.87 g, 60%).

Workup

  1. stirringThe resulting mixture was stirred for 1 h at -78° C.
  2. customThe reaction was quenched with water
  3. extractionextracted with EtOAc (2×50 mL)
  4. washThe combined organic extracts were washed with H2O, brine
  5. dry with materialdried (MgSO4)
  6. customAfter removing the solvent under reduced pressure, column chromatography (silica gel, EtOAc/Hexane, 20:80) of the residue

Sources & evidence

ORD record
ord-5603aa86c7d14cf6aea3b963e8eb3b67
Source dataset
uspto-grants-2000_01
Patent number
US06017952

Linked notes

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