1-methyl-1H-imidazole-5-carbaldehyde → (1-Methyl-1H-imidazol-5-yl)(4-(tetrahydro-2H-pyran-2-yloxy)phenyl)methanol

HRID 2246652Notes

Reaction equation

[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][C:8]1[CH:13]=[CH:12][C:11]([Mg]Br)=[CH:10][CH:9]=1.[CH3:16][N:17]1[C:21]([CH:22]=[O:23])=[CH:20][N:19]=[CH:18]1>C1COCC1>[CH3:16][N:17]1[C:21]([CH:22]([C:11]2[CH:12]=[CH:13][C:8]([O:7][CH:2]3[CH2:3][CH2:4][CH2:5][CH2:6][O:1]3)=[CH:9][CH:10]=2)[OH:23])=[CH:20][N:19]=[CH:18]1

Participants

Conditions

Temperature: -78 °C

Procedure

4-(2-Tetrahydro-3H-pyranoxy)phenylmagnesium bromide (110 mL, 0.5 M in THF, 55 mmol) was added dropwise to a solution of 1-methyl-1H-imidazole-5-carbaldehyde (4.7 g, 50 mmol) in THF (790 mL) at −78° C. After stirring −78° C. for 2 hours, the reaction was quenched with saturated NH4Cl (aq) and warmed to room temperature. The mixture was extracted with EtOAc (500 mL), and the organic phase was washed with water and brine, dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to give 14 g of the crude product 4.1, which was used in the next reaction without further purification.

Workup

customthe reaction was quenched with saturated NH4Cl (aq)
temperaturewarmed to room temperature
extractionThe mixture was extracted with EtOAc (500 mL)
washthe organic phase was washed with water and brine
dry with materialdried over anhydrous sodium sulfate
filtrationfiltered
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-b509942a6af4414fb949ed91d3309c4d
Source dataset: uspto-grants-2010_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07687526B2

Reaction notes

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