Dimethylformamide → HCID 19429697, compound

HRID 1078507Notes

Reaction equation

HRID 1078507 reaction equation
[Mg].[Si:2]([O:9][C:10]1[CH:15]=[CH:14][C:13](Br)=[CH:12][C:11]=1[C:17]1([CH3:23])[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1)([C:5]([CH3:8])([CH3:7])[CH3:6])([CH3:4])[CH3:3].CN([CH:27]=[O:28])C>BrC(Br)C.O>[Si:2]([O:9][C:10]1[CH:15]=[CH:14][C:13]([CH:27]=[O:28])=[CH:12][C:11]=1[C:17]1([CH3:23])[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1)([C:5]([CH3:8])([CH3:7])[CH3:6])([CH3:4])[CH3:3]

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 5462224MagnesiumHCID 10500173HCID 10500173, compound

Product 1

HCID 19429697HCID 19429697, compound

Reagents, catalysts & solvents 2

HCID 112011,1-DibromoethaneCatalystHCID 962WaterSolvent

Procedure

1.54 g of magnesium are placed in a 500 ml three-necked round-bottomed flask and then a solution containing 22.09 g (57.7 mmol) of 4-tert-butyldimethylsilyloxy-3-(1-methylcyclohexyl)bromobenzene is added through a dropping funnel. The reaction is activated by a few drops of dibromoethane. 4.45 ml (57 mmol) of DMF are then added and the mixture is left stirring for 30 min at room temperature. The reaction medium is poured into water and then extracted with ethyl acetate. After rinsing the organic phase with water, drying over magnesium sulphate, evaporation and chromatography on silica in the dichloromethane/hexane eluent (50/50), 16 g (84%) of the expected derivative are isolated.

Workup

  1. additionis added through a dropping funnel
  2. waitthe mixture is left
  3. extractionextracted with ethyl acetate
  4. washAfter rinsing the organic phase with water
  5. dry with materialdrying over magnesium sulphate, evaporation and chromatography on silica in the dichloromethane/hexane eluent (50/50), 16 g (84%) of the expected
  6. customderivative are isolated

Sources & evidence

ORD record
ord-be1b0623c62e406cb22cf1402d1dc242
Source dataset
uspto-grants-1996_08
Patent number
US05547983

Reaction notes

Loading…