Aluminium lithium hydride → (1-Cyclopropyl-2,5-dimethyl-1H-imidazol-4-yl)-methanol

HRID 8894

Reaction equation

C([O:3][C:4]([C:6]1[N:7]=[C:8]([CH3:15])[N:9]([CH:12]2[CH2:14][CH2:13]2)[C:10]=1[CH3:11])=O)C.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[CH:12]1([N:9]2[C:10]([CH3:11])=[C:6]([CH2:4][OH:3])[N:7]=[C:8]2[CH3:15])[CH2:14][CH2:13]1

Participants

Conditions

Temperature: 0 °C

Procedure

Cyclopropyl-2,5-dimethyl-1H-imidazole-4-carboxylic acid ethyl ester (0.7 g, 3 mmol) was dissolved in 20 mL dry THF and cooled to 0° C. Lithium aluminum hydride (3.4 mL, 1M in THF, 3 mmol) was added dropwise and stirred for 1 h at 0° C. The reaction mixture was quenched with 0.13 ml of water, 0.13 ml of 4N sodium hydroxide and 0.4 ml of water. Sodium sulfate was added, stirred for 10 min, filtered and evaporated to dryness to obtain the desired compound as a light yellow solid (0.52 g, 93%), MS: m/e=167.4 (M+H)+.

Workup

customThe reaction mixture was quenched with 0.13 ml of water, 0.13 ml of 4N sodium hydroxide and 0.4 ml of water
additionSodium sulfate was added
stirringstirred for 10 min
filtrationfiltered
customevaporated to dryness

Sources & evidence

ORD record: ord-aa284e86cc9240c4ba4ba2f67db199c4
Source dataset: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07091222B2

Linked notes

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