Butyl bromide → HCID 20279069, compound

HRID 1248198Notes

Reaction equation

HRID 1248198 reaction equation
[CH:1]1([CH2:7][CH2:8][C:9](=O)[CH2:10][N:11]2[CH:15]=[CH:14][N:13]=[CH:12]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:17]([Mg]Br)[CH2:18][CH2:19][CH3:20].C(Br)CCC.[Mg].[O:29]1CCCC1>>[CH:1]1([CH2:7][C:8]([OH:29])([CH2:17][CH2:18][CH2:19][CH3:20])[CH2:9][CH2:10][N:11]2[CH:15]=[CH:14][N:13]=[CH:12]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 5

HCID 8002Butyl bromideHCID 8028Tetrahydrofuran2×HCID 5462224MagnesiumHCID 20279088HCID 20279088, compoundHCID 178418682HCID 178418682, compound

Product 1

HCID 20279069HCID 20279069, compound

Procedure

1-[4-Cyclohexyl-2-oxo-n-butyl]imidazole (2.2 g) in 15 ml of dry tetrahydrofuran was added dropwise to a stirred solution of butylmagnesium bromide [from butyl bromide (2.05 g) and magnesium (0.36 g)]in 20 ml of tetrahydrofuran at 0° C. under nitrogen. After one hour the mixture was allowed to come to room temperature and quenched with saturated ammonium chloride. Most of the tetrahydrofuran was removed under reduced pressure and the residue treated with aqueous potassium carbonate and extracted with ethyl acetate. The extracts were washed, dried (MgSO4) and evaporated to give 1-[3-(cyclohexylmethyl)-3-hydroxy-n-heptyl]imidazole. Purification could be effected if needed by chromatographpy on silica gel eluting with 5% methanol in methylene chloride.

Workup

  1. customto come to room temperature
  2. customquenched with saturated ammonium chloride
  3. customMost of the tetrahydrofuran was removed under reduced pressure
  4. additionthe residue treated with aqueous potassium carbonate
  5. extractionextracted with ethyl acetate
  6. washThe extracts were washed
  7. dry with materialdried (MgSO4)
  8. customevaporated

Sources & evidence

ORD record
ord-354dcf47e9174273b827a428ec5cc0c9
Source dataset
uspto-grants-1985_06
Patent number
US04522948

Reaction notes

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