Water → (1-(tetrahydro-2H-pyran-2-yl)-1H-benzo[d]imidazol-5-yl)methanol

HRID 475173Notes

Reaction equation

[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[N:7]1[C:11]2[CH:12]=[CH:13][C:14]([C:16](OC)=[O:17])=[CH:15][C:10]=2[N:9]=[CH:8]1.[H-].[H-].[H-].[H-].[Li+].[Al+3].O.[OH-].[Na+]>C1COCC1>[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[N:7]1[C:11]2[CH:12]=[CH:13][C:14]([CH2:16][OH:17])=[CH:15][C:10]=2[N:9]=[CH:8]1

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 22 (2.5 g, 9.61 mmol) in anhydrous THF (10 mL) was added dropwise to a mixture of LiAlH4 (0.55 g, 14.42 mmol) in anhydrous THF (20 mL) at 0° C. under nitrogen. The reaction mixture was stirred for 30 min at 0° C. then treated sequentially with water (2 mL) and 10% NaOH (1.8 mL). The resulting mixture was extracted with ether (2×100 mL). The combined organic layers were dried (Na2SO4), filtered and concentrated in vacuo to afford 2.24 g (95%) of (1-(tetrahydro-2H-pyran-2-yl)-1H-benzo[d]imidazol-5-yl)methanol (24) as yellow oil: MS (ESI) m/z=233.2 [M+1]+.

Workup

extractionThe resulting mixture was extracted with ether (2×100 mL)
dry with materialThe combined organic layers were dried (Na2SO4)
filtrationfiltered
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-b105b8d8ad87430ca0e5f137e1fd7d4c
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08637537B2

Reaction notes

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