Ammonium Chloride → HCID 54030506, compound

HRID 2106661Notes

Reaction equation

HRID 2106661 reaction equation
[Mg].[CH:2]1(Br)[CH2:4][CH2:3]1.[CH3:6][N:7]1[CH:11]=[CH:10][CH:9]=[C:8]1[C:12]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:13].[Cl-].[NH4+]>O1CCCC1.O>[CH:2]1([C:12]([C:8]2[N:7]([CH3:6])[CH:11]=[CH:10][CH:9]=2)([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[OH:13])[CH2:4][CH2:3]1

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 78037BromocyclopropaneHCID 142165Methanone, (1-methyl-1H-pyrrol-2-yl)phenyl-HCID 5462224Magnesium

Product 1

HCID 54030506HCID 54030506, compoundYield 60.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent3×

Procedure

To a suspension of magnesium turnings (5.29 g, 0.22 mole) in anhydrous tetrahydrofuran (70 ml), cyclopropyl bromide (26.35 g, 0.22 mole) in tetrahydrofuran (50 ml) was added dropwise under nitrogen. The reaction mixture was heated at reflux for one h after the initial exotherm had subsided before (N-methylpyrrol-2-yl)phenylketone (13.3 g, 0.072 mole) (J. White and G. McGillivray, J. Org. Chem., (1977), 42, 4248, R. Greenhouse and C. Ramirez, J. Org. Chem., (1985), 50, 2961) in anhydrous tetrahydrofuran (50 ml ) was introduced dropwise. After heating the reaction mixture at reflux for 3 h it was cooled and saturated, aqueous ammonium chloride solution (95 ml) and water (150 ml) were added. The mixture was extracted with ethyl acetate (3×200 ml) and the combined extracts were dried (MgSO4). Flash chromatography of the residue on evaporation on silica gel eluting with heptane/tetrahydrofuran (9:1) provided the title compound as an oil (9.9 g, 46%) which solidified on standing. T.l.c. rf=0.35 (SiO2, heptane/THF (7:3)).

Workup

  1. additionwas added dropwise under nitrogen
  2. temperatureThe reaction mixture was heated
  3. temperatureat reflux for one h after the initial exotherm
  4. additionwas introduced dropwise
  5. temperatureAfter heating the reaction mixture
  6. temperatureat reflux for 3 h it
  7. temperaturewas cooled
  8. extractionThe mixture was extracted with ethyl acetate (3×200 ml)
  9. dry with materialthe combined extracts were dried (MgSO4)
  10. customFlash chromatography of the residue on evaporation on silica gel eluting with heptane/tetrahydrofuran (9:1)

Sources & evidence

ORD record
ord-7d0c67b2149443dd865dce9f48155100
Source dataset
uspto-grants-1990_06
Patent number
US04931450

Reaction notes

Loading…