N,N,N',N'-Tetramethylethylenediamine → alpha-(o-tert.-Butylphenyl)-1-(methoxymethyl)-alpha-phenylimidazole-2-methanol

HRID 261958Notes

Reaction equation

HRID 261958 reaction equation
C([Li])CCC.CN(C)CCN(C)C.[CH3:14][O:15][CH2:16][N:17]1[CH:21]=[CH:20][N:19]=[CH:18]1.[C:22]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[C:32](=[O:39])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)([CH3:25])([CH3:24])[CH3:23]>O1CCCC1>[C:22]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[C:32]([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)([C:18]1[N:17]([CH2:16][O:15][CH3:14])[CH:21]=[CH:20][N:19]=1)[OH:39])([CH3:25])([CH3:23])[CH3:24]

Participants

6

Reactant 4

HCID 8037N,N,N',N'-TetramethylethylenediamineHCID 883591-(methoxymethyl)-1H-imidazoleHCID 54101900(2-tert-Butylphenyl)(phenyl)methanoneHCID 178418339Butyllithium

Product 1

HCID 12433889alpha-(o-tert.-Butylphenyl)-1-(methoxymethyl)-alpha-phenylimidazole-2-methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Under a nitrogen atmosphere and at -60° C., 38 ml. (0.08 mol) of a butyllithium solution (20% in n-hexane) were added drop-wise over the course of 45 minutes to a mixture of 9.6 g. (0.08 mol) of N,N,N',N'-tetramethylethylenediamine and 7 g. (0.06 mol) of 1-(methoxymethyl)imidazole in 100 ml. of anhydrous tetrahydrofuran. The mixture was stirred for another two hours under the same conditions and then 16 g (0.0675 mol) of o-tert.-butylbenzophenone in 100 ml. of anhydrous tetrahydrofuran were added dropwise. After the addition was completed, the mixture was stirred for 2 hours at -60° C., and one hour at room temperature. The mixture was decomposed with 5 ml. of water, the precipitate was filtered off and the filtrate was dried over sodium sulphate and concentrated. The solid residue was crystallised from isopropyl alcohol. α-(o-tert.-Butylphenyl)-1-(methoxymethyl)-α-phenylimidazole-2-methanol was obtained. Melting point 149°-150° C.

Workup

  1. customat -60° C.
  2. additionto a mixture of 9.6 g
  3. additionAfter the addition
  4. stirringthe mixture was stirred for 2 hours at -60° C.
  5. customone hour
  6. customat room temperature
  7. filtrationof water, the precipitate was filtered off
  8. dry with materialthe filtrate was dried over sodium sulphate
  9. concentrationconcentrated
  10. customThe solid residue was crystallised from isopropyl alcohol

Sources & evidence

ORD record
ord-bcde5cfa3a484f71b99c2e2da89ec4cc
Source dataset
uspto-grants-1979_05
Patent number
US04152441

Reaction notes

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