N,N,N',N'-Tetramethylethylenediamine → alpha,alpha-Bis(p-tert.-butylphenyl)-1-vinylimidazole-2-methanol

HRID 261955

Reaction equation

HRID 261955 reaction equation
[C:1]([C:5]1[CH:22]=[CH:21][C:8]([C:9]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([CH3:20])([CH3:19])[CH3:18])=[CH:13][CH:12]=2)=[O:10])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C([Li])CCC.[CH:28]([N:30]1[CH:34]=[CH:33][N:32]=[CH:31]1)=[CH2:29].CN(C)CCN(C)C>CCCCCC>[C:17]([C:14]1[CH:13]=[CH:12][C:11]([C:9]([C:8]2[CH:21]=[CH:22][C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])=[CH:6][CH:7]=2)([C:31]2[N:30]([CH:28]=[CH2:29])[CH:34]=[CH:33][N:32]=2)[OH:10])=[CH:16][CH:15]=1)([CH3:20])([CH3:19])[CH3:18]

Participants

6

Reactant 4

HCID 8037N,N,N',N'-TetramethylethylenediamineHCID 661711-VinylimidazoleHCID 2758048Bis(4-tert-butylphenyl)methanoneHCID 178418339Butyllithium

Product 1

HCID 12433927alpha,alpha-Bis(p-tert.-butylphenyl)-1-vinylimidazole-2-methanol

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

This compound was prepared by the procedure indicated in Example XXII A, using the following materials: 10 g. (0.03 mol) of 4,4'-di-tert.-butylbenzophenone, 19.5 ml. (0.04 mol) of 20% butyllithium in n-hexane, 3 g. (0.03 mol) of 1-vinylimidazole and 4.9 g. (0.04 mol) of N,N,N', N'-tetramethylethylenediamine. The product was crystallised from ethyl acetate. Melting point 169°-170° C.

Workup

  1. customThis compound was prepared by the procedure
  2. customThe product was crystallised from ethyl acetate

Sources & evidence

ORD record
ord-55a25409996f478bbdcc1ae6f54a693a
Source dataset
uspto-grants-1979_05
Patent number
US04152441

Linked notes

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