ChemicalBook CAS DataBase List (1-METHYL-1H-IMIDAZOL-5-YL)METHANOL

(1-METHYL-1H-IMIDAZOL-5-YL)METHANOL synthesis

12synthesis methods

Product Name:(1-METHYL-1H-IMIDAZOL-5-YL)METHANOL
CAS Number:38993-84-9
Molecular formula:C5H8N2O
Molecular Weight:112.13

66787-70-0
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38993-84-9
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Yield: 73%

Reaction Conditions:

with lithium aluminium tetrahydride in tetrahydrofuran at 20; for 16 h;

Steps:

8
S-Methyl-SH-imidazole^-carboxylic acid ethyl ester (Chem. Pharm. Bull, 1994, 42,1463) (0.62 g, 4.02 mmol) in THF (5mL) was added dropwise over 1 min. to a slurry of lithium aluminum hydride (0.25 g, 6.60 mmol) in THF (20 mL). After stirring 16h at room temperature, the reaction was carefully quenched with excess sodium sulfate decahydrate, dried with anhydrous sodium sulfate and filtered through Celite. Concentration gave 0.33 g (73%) of (3- methyl-3H-imidazol-4-yl)-methanol as a white solid which had: NMR (CDCI₃) δ 7.38 (s, 1 H), 6.87 (s, 1 H), 4.60 (s, 2H)₁ 3.69 (s, 3H). A solution of this alcohol (0.150 g, 1.34 mmol) in thionyl chloride (5 mL) was refluxed for 3 h and concentrated. The residue was dissolved in a minimum of ethanol and ether was added to precipitate a white solid. This was collected to yield 0.185 g (83%) of 5-chloromethyl-1-methyl-1H-imidazole hydrochloride which had: NMR (DMSOd₆) δ 9.15 (s, 1 H), 7.75 (d, J = 1.2 Hz, 1 H), 4.99 (s, 2H), 3.84 (s, 3H).

References:

PFIZER PRODUCTS INC. WO2007/34277, 2007, A1 Location in patent:Page/Page column 58