Water → HCID 86650592, compound

HRID 1257394Notes

Reaction equation

HRID 1257394 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH2:8][C:9]1[N:10]=[C:11]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:23])([F:22])[F:21])[CH:15]=2)[S:12][CH:13]=1.C([Li])CCC.CN(C)[CH:31]=[O:32].O>O1CCCC1>[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH2:8][C:9]1[N:10]=[C:11]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:23])([F:21])[F:22])[CH:15]=2)[S:12][C:13]=1[CH:31]=[O:32]

Participants

6

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 66939482HCID 66939482, compoundHCID 178418339Butyllithium

Product 1

HCID 86650592HCID 86650592, compoundYield 64.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under a nitrogen atmosphere at −78° C., to a solution (100 mL) of the compound (8.0 g, 23 mmol) obtained in Example 89a in tetrahydrofuran was added n-butyllithium (1.6M hexane solution, 18 mL, 28 mmol), and the mixture was stirred at the same temperature for 1 hr. Anhydrous N,N-dimethylformamide (2.3 mL, 30 mmol) was added to the reaction mixture, and the mixture was stirred at −78° C. for 3 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The resulting crude title compound was purified by column chromatography (hexane-hexane/ethyl acetate=80/20) to give the title compound (5.5 g, 64%) as a pale-yellow solid.

Workup

  1. stirringthe mixture was stirred at −78° C. for 3 hr
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe obtained organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customThe resulting crude title compound was purified by column chromatography (hexane-hexane/ethyl acetate=80/20)

Sources & evidence

ORD record
ord-4f2d25e12daa4ca8a78b6153ee3adaba
Source dataset
uspto-grants-2013_06
Patent number
US08461348B2

Reaction notes

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