Hydrochloric Acid → 1-[4-[1-(1-Imidazolyl)-butyl]-phenyl]-ethanol

HRID 727849Notes

Reaction equation

HRID 727849 reaction equation
[N:1]1([CH:6]([C:10]2[CH:17]=[CH:16][C:13]([CH2:14][OH:15])=[CH:12][CH:11]=2)[CH2:7][CH2:8][CH3:9])[CH:5]=[CH:4][N:3]=[CH:2]1.[CH3:18][Mg]Br.O1CCCC1.Cl>CCOCC>[N:1]1([CH:6]([C:10]2[CH:11]=[CH:12][C:13]([CH:14]([OH:15])[CH3:18])=[CH:16][CH:17]=2)[CH2:7][CH2:8][CH3:9])[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 145143764-[1-(1-Imidazolyl)-butyl]-benzyl alcoholHCID 178418573HCID 178418573, compound

Product 1

HCID 198251771-[4-[1-(1-Imidazolyl)-butyl]-phenyl]-ethanol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

460 mg of the aldehyde of example 5 in 8 ml of ether is mixed with 1.5 ml of a 3M methyl magnesium bromide solution in ether with ice cooling and is stirred for 20 hours at room temperature; 10 ml of tetrahydrofuran is added and heated to 60° C. in 6 hours. It is added to 1M of hydrochloric acid, extracted with ether, then the water phase is alkalized with potassium carbonate and extracted with ether. After drying and concentration by evaporation of this ether phase, the residue is chromatographed on silica gel (methylene chloride/methanol (95:5)). 300 mg of the title compound is obtained.

Workup

  1. temperatureheated to 60° C. in 6 hours
  2. extractionextracted with ether
  3. extractionextracted with ether
  4. customAfter drying
  5. concentrationconcentration
  6. customby evaporation of this ether phase
  7. customthe residue is chromatographed on silica gel (methylene chloride/methanol (95:5))

Sources & evidence

ORD record
ord-a773e42e0ebb4870bcd6bbe0cf1d3915
Source dataset
uspto-grants-1991_09
Patent number
US05045558

Reaction notes

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