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

HRID 262607

Reaction equation

[CH2:1]([Li])[CH2:2][CH2:3]C.C=O.[OH:8][CH2:9][C:10]1[N:14]2CCCCC2=[CH:12][N:11]=1>>[CH3:12][N:11]1[CH:3]=[C:2]([CH3:1])[N:14]=[C:10]1[CH2:9][OH:8]

Participants

Reactant 3

HCID 712Formaldehyde

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-dimethylamidazole (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 in Example 243) gave 1,4-dimethyl-2-hydroxymethylimidazole (2.71 g.), m.p. 125°-126° (ethyl acetate-petroleum ether).

Sources & evidence

ORD record: ord-600d33573d3948dab7ef1f782a87ba80
Source dataset: uspto-grants-1979_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04154844

Linked notes

Loading…