HCID 9860843, compound → HCID 9795740, compound

HRID 380979Notes

Reaction equation

HRID 380979 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH3:15])[CH2:9][NH:10][S:11]([CH3:14])(=[O:13])=[O:12])=[CH:4][CH:3]=1.[CH:16]1([Mg]Br)[CH2:20][CH2:19][CH2:18][CH2:17]1>O1CCCC1>[CH:16]1([C:2]2[CH:7]=[CH:6][C:5]([CH:8]([CH3:15])[CH2:9][NH:10][S:11]([CH3:14])(=[O:13])=[O:12])=[CH:4][CH:3]=2)[CH2:20][CH2:19][CH2:18][CH2:17]1

Participants

4

Reactant 2

HCID 9860843HCID 9860843, compoundHCID 178419650HCID 178419650, compound

Product 1

HCID 9795740HCID 9795740, compoundYield 13%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Condition 1: The product of Example 1, 0.50 g (1.71 mmol) was dissolved in anhydrous tetrahydrofuran (5 ml) under an atmosphere of nitrogen. To this was added tetrakis-(triphenylphosphine)palladium(0) (0.099 g, 0.086 mmol) followed by cyclopentyl magnesium bromide (2 M in diethyl ether, 2.14 ml, 4.28 mmol). The solution was heated to reflux for 16 hours. Upon cooling the reaction was partitioned between water and diethyl ether. The aqueous layer was back extracted with diethyl ether twice and the organic fractions combined. The organic layers were washed with brine, dried (MgSO4) and concentrated in vacuo. Chromatography (Sio2, 30% ethyl acetate/hexanes) gave the title compound 0.06 g (13%).

Workup

  1. temperatureThe solution was heated
  2. temperatureto reflux for 16 hours
  3. temperatureUpon cooling the reaction
  4. customwas partitioned between water and diethyl ether
  5. extractionThe aqueous layer was back extracted with diethyl ether twice
  6. washThe organic layers were washed with brine
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6fc7a7791b4b4218b4dbda98ef789293
Source dataset
uspto-grants-2001_10
Patent number
US06303816B1

Reaction notes

Loading…