Tetrahydrofuran → HCID 85937151, compound

HRID 2252050Notes

Reaction equation

HRID 2252050 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:12]=[C:13]([F:15])[CH:14]=1)[O:5][CH2:6]N1CCCC1.[O:16]1[CH2:20]CCC1.[CH2:21]([Li])[CH2:22][CH2:23][CH3:24].[CH3:26][N:27](C)CCN(C)C>CN(C)C=O>[F:15][C:13]1[CH:12]=[C:4]([O:5][CH2:6][CH2:26][N:27]2[CH2:24][CH2:23][CH2:22][CH2:21]2)[CH:3]=[C:2]([F:1])[C:14]=1[CH:20]=[O:16]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 8037N,N,N',N'-TetramethylethylenediamineHCID 19002669HCID 19002669, compoundHCID 178418339Butyllithium

Product 1

HCID 85937151HCID 85937151, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Cool a mixture of 1-(3,5-difluoro-phenoxymethyl)-pyrrolidine (0.1 g) and dry tetrahydrofuran (5 mL) to −78° C. under a nitrogen atmosphere. Add butyllithium (0.29 mL, 1.6 M in tetrahydrofuran) and N,N,N′,N′-tetramethylethylenediamine (0.5 mL) and stir for 30 minutes. Then, add dimethylformamide (0.07 mL) and stir at room temperature for 60 minutes. Quench by pouring the reaction mixture into a mixture of cold saturated aqueous ammonium chloride and ethyl acetate. Separate the layers, wash the organic phase with water and then concentrate under reduced pressure to provide (0.10 g, 94%) of the title compound as an oil.

Workup

  1. temperatureCool
  2. customQuench
  3. additionby pouring the reaction mixture
  4. additioninto a mixture of cold saturated aqueous ammonium chloride and ethyl acetate
  5. customSeparate the layers
  6. washwash the organic phase with water
  7. concentrationconcentrate under reduced pressure

Sources & evidence

ORD record
ord-5e55c9512a2b4eb59fadc90566747e26
Source dataset
uspto-grants-2008_01
Patent number
US07320995B2

Reaction notes

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