Formaldehyde → (1,4-dimethyl-1H-imidazol-2-yl)methanol

HRID 26826

Reaction equation

[CH3:1][N:2]1[CH:6]=[C:5]([CH3:7])[N:4]=[CH:3]1.C([Li])CCC.C=O.[OH:15][CH2:16]C1N2CCCCC2=CN=1>>[CH3:1][N:2]1[CH:6]=[C:5]([CH3:7])[N:4]=[C:3]1[CH2:16][OH:15]

Participants

Reactant 4

HCID 712Formaldehyde

HCID 1387331,4-Dimethylimidazole

HCID 12923422(5,6,7,8-Tetrahydroimidazo[1,5-a]pyridin-3-yl)methanol

HCID 178418339Butyllithium

Product 1

HCID 12923402(1,4-dimethyl-1H-imidazol-2-yl)methanol

Procedure

The reaction of 1,4-dimethylimidazole (5.65 g.) with n-butyl lithium followed by treatment with formaldehyde according to the method described for the preparation of 3-hydroxymethyl-5,6,7,8-tetrahydroimidazo[1,5-a]pyridine (used for Example 224) gave 1,4-dimethyl-2-hydroxymethylimidazole (2.71 g.), m.p. 125°-126° (ethyl acetate-petroleum ether).

Sources & evidence

ORD record: ord-40b7f1f82e30499792fc93ed94a768b2
Source dataset: uspto-grants-1979_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04151288

Linked notes

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