Ethyl Acetate → HCID 59678697, compound

HRID 1751870Notes

Reaction equation

HRID 1751870 reaction equation
[C:1]([N:5]1[C:10](=[O:11])[C:9]([CH2:12][O:13][Si:14]([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15])=[C:8](Cl)[CH:7]=[N:6]1)([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[Cs+].[Cs+].[C:28]([C:32]1[CH:39]=[CH:38][C:35]([CH2:36][SH:37])=[CH:34][CH:33]=1)([CH3:31])([CH3:30])[CH3:29].C(OCC)(=O)C>CN(C=O)C>[C:1]([N:5]1[C:10](=[O:11])[C:9]([CH2:12][O:13][Si:14]([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15])=[C:8]([S:37][CH2:36][C:35]2[CH:38]=[CH:39][C:32]([C:28]([CH3:31])([CH3:30])[CH3:29])=[CH:33][CH:34]=2)[CH:7]=[N:6]1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 27572524-tert-Butylbenzyl mercaptanHCID 59678615HCID 59678615, compound

Product 1

HCID 59678697HCID 59678697, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 2-tert-butyl-4-tert-butyldimethylsilyloxymethyl-5-chloro 3(2H)-pyridazinone (1.5 g, 4.54 mmol) in DMF (10 ml) is added anhydrous cesium carbonate (2.9 g, 9.09 mmol) and 4-tert-butybenzyl mercaptan (1.02 g, 4.54 mmol). The mixture is stirred for 2 hours at 70° C. and then cooled to room temperature and ethyl acetate is added to it. The solution is then washed with water, dried and concentrated and the residue subjected to purification by flash chromatography (silica gel; ethyl acetate/hexanes) to give the above compound.

Workup

  1. temperaturecooled to room temperature
  2. washThe solution is then washed with water
  3. customdried
  4. concentrationconcentrated
  5. customthe residue subjected to purification by flash chromatography (silica gel; ethyl acetate/hexanes)
  6. customto give the above compound

Sources & evidence

ORD record
ord-1626f8f7ff5c4f1590d3af07ab0d0a92
Source dataset
uspto-grants-2015_10
Patent number
US09161997B2

Reaction notes

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