Dimethylformamide → 55745-99-8

HRID 926998Notes

Reaction equation

HRID 926998 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[S:8][CH2:7][CH2:6][CH2:5]2.C([Li])CCC.CCCCCC.CN([CH:26]=[O:27])C.[Cl-].[NH4+]>C1COCC1>[S:8]1[C:9]2[C:4](=[CH:3][C:2]([CH:26]=[O:27])=[CH:11][CH:10]=2)[CH2:5][CH2:6][CH2:7]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 25517Ammonium ChlorideHCID 19702076109209-87-2HCID 178418244HCID 178418244, compound

Product 1

HCID 5366560555745-99-8

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

6-Bromo-thiochromane (1.00 g) was dissolved in THF (15.0 mL), added dropwise with 2.69 mol/L n-butyl lithium/hexane solution (3.24 mL) at −78° C., and stirred for 1 hour at the same temperature. After adding DMF (0.71 mL) at the same temperature, it was stirred for 16 hours while raising the temperature to room temperature. A saturated aqueous solution of ammonium chloride was added, and after extraction with ethyl acetate, the organic layer was washed with saturated brine. After drying over anhydrous sodium sulfate, the solvent was evaporated under reduced pressure and the residues were purified by silica gel column chromatography (2 to 15% ethyl acetate/hexane) to obtain the title compound (342 mg) as a colorless oil.

Workup

  1. stirringwas stirred for 16 hours
  2. extractionafter extraction with ethyl acetate
  3. washthe organic layer was washed with saturated brine
  4. dry with materialAfter drying over anhydrous sodium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customthe residues were purified by silica gel column chromatography (2 to 15% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-24ffe5624ac74a2e85ec8d5131567a94
Source dataset
uspto-grants-2016_03
Patent number
US09290440B2

Reaction notes

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