Water → 5-(1H-imidazol-1-yl)-2-methoxybenzenemethanol

HRID 650046Notes

Reaction equation

[N:1]1([C:6]2[CH:7]=[CH:8][C:9]([O:16][CH3:17])=[C:10]([CH:15]=2)[C:11](OC)=[O:12])[CH:5]=[CH:4][N:3]=[CH:2]1.[H-].[H-].[H-].[H-].[Li+].[Al+3].O.[OH-].[Na+]>C1COCC1>[N:1]1([C:6]2[CH:7]=[CH:8][C:9]([O:16][CH3:17])=[C:10]([CH2:11][OH:12])[CH:15]=2)[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

Conditions

Temperature: 24 °C

Procedure

5-(1H-Imidazol-1-yl)-2-methoxybenzoic acid, methyl ester (2 g, 8.6 mmol) was cooled to 0C in anhydrous THF under N2 and LiAlH4 was added. The reaction mixture stirred for 18 h at 24° C,. and water (0.7 ml) followed 15% sodium hydroxide solution (0.7 ml) and water (0.7 ml) was sequentially added dropwise. The resultant suspension was filtered and concentrated to give 1.3 g (74%); 1H NMR (300 MHz, DMSO-d6) δ 3.81(3H, s), 4.52 (2H, d, J=4.3 Hz), 5.18 (1H, br. s), 7.04 -7.06 (2H, m), 7.43 (1H, dd, J=8.7 Hz, 2.8 Hz), 7.52 (1H, d, J=2.8 Hz) 7.58 (1H, s), 8.07 (1H, s); MS(DCl)m/z: 205 (MH+).

Workup

additionwas sequentially added dropwise
filtrationThe resultant suspension was filtered
concentrationconcentrated
customto give 1.3 g (74%)

Sources & evidence

ORD record: ord-fb871d98766a4ba5ab086f42fc346da7
Source dataset: uspto-grants-2001_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06271249B1

Reaction notes

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