HCID 178418573, compound → HCID 178467221, compound

HRID 1863422Notes

Reaction equation

HRID 1863422 reaction equation
[CH3:1][Mg]Br.[C:4]1([C:10]2[NH:11][CH:12]=[C:13]([CH:15]=[O:16])[N:14]=2)[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>O1CCCC1>[CH3:1][CH:15]([C:13]1[N:14]=[C:10]([C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=2)[NH:11][CH:12]=1)[OH:16]

Participants

4

Reactant 2

HCID 178418573HCID 178418573, compoundHCID 178519858HCID 178519858, compound

Product 1

HCID 178467221HCID 178467221, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

Methyl magnesium bromide (15.3 ml., 2.5 molar in ether) is added dropwise to a solution of 2-phenyl-4-imidazolecarboxaldehyde (3.0 gm. 0.017 mole) in dry tetrahydrofuran (45 ml.; dried over a molecular sieve) while the temperature of the reaction mixture is maintained with cooling at 25° C. The mixture is stirred for 2 hours, and then decomposed by adding a large volume of water dropwise. The mixture is extracted with ether (3×75 ml.), the ethereal extract is partially evaporated to yield a white precipitate, the crystalline alcohol, m.p. 197°-198° C.

Workup

  1. customdried over a molecular sieve) while the temperature of the reaction mixture
  2. temperatureis maintained
  3. additionby adding a large volume of water dropwise
  4. extractionThe mixture is extracted with ether (3×75 ml.)
  5. extractionthe ethereal extract
  6. customis partially evaporated
  7. customto yield a white precipitate

Sources & evidence

ORD record
ord-689f6f5ab5914bf6a00997d0a84b516b
Source dataset
uspto-grants-1979_09
Patent number
US04168964

Reaction notes

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