Methyl vinyl sulfone → HCID 89498322, compound

HRID 1778926Notes

Reaction equation

HRID 1778926 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][N:5]([CH2:8][C:9]2([OH:17])[CH2:14][CH2:13][CH2:12][C:11]([CH3:16])([CH3:15])[CH2:10]2)[C:6]=1[CH3:7].[H-].[Na+].[CH3:20][S:21]([CH:24]=[CH2:25])(=[O:23])=[O:22]>O1CCCC1.C(OCC)(=O)C>[Br:1][C:2]1[CH:3]=[N:4][N:5]([CH2:8][C:9]2([O:17][CH2:25][CH2:24][S:21]([CH3:20])(=[O:23])=[O:22])[CH2:14][CH2:13][CH2:12][C:11]([CH3:15])([CH3:16])[CH2:10]2)[C:6]=1[CH3:7]

Participants

6

Reactant 3

HCID 19354Methyl vinyl sulfoneHCID 24758Sodium hydrideHCID 89498386HCID 89498386, compound

Product 1

HCID 89498322HCID 89498322, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of EXAMPLE 157B (0.218 g) in tetrahydrofuran (2.5 mL) was added sodium hydride (0.027 g) and the reaction mixture was stirred for 15 minutes at room temperature. Methylsulfonylethene (0.095 mL) was added and the reaction was stirred at room temperature overnight. The reaction was cooled and diluted with ethyl acetate (50 mL). The organic layer was washed with water (50 mL) and brine (50 mL), dried over magnesium sulfate, filtered, and concentrated. Silica gel chromatography eluting with a gradient of 1-20% ethyl acetate in hexanes provided the title compound.

Workup

  1. stirringthe reaction was stirred at room temperature overnight
  2. temperatureThe reaction was cooled
  3. washThe organic layer was washed with water (50 mL) and brine (50 mL)
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. washSilica gel chromatography eluting with a gradient of 1-20% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-dd97cf90b32046ffa96fdcc1300c6001
Source dataset
uspto-grants-2016_02
Patent number
US09266877B2

Reaction notes

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