Water → 2-(2-Propylimidazol-1-yl)propan-1-ol

HRID 981524Notes

Reaction equation

[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([C:10]1[N:11]([CH:15]([CH3:21])[C:16](OCC)=[O:17])[CH:12]=[CH:13][N:14]=1)[CH2:8][CH3:9].O.[OH-].[Na+]>O1CCCC1>[CH2:7]([C:10]1[N:11]([CH:15]([CH3:21])[CH2:16][OH:17])[CH:12]=[CH:13][N:14]=1)[CH2:8][CH3:9]

Participants

Conditions

Temperature: 0 °C

Procedure

Lithium aluminum hydride (2.5 g) was suspended in tetrahydrofuran (40 ml). Ethyl 2-(2-propylimidazol-1-yl)propanate [9.2 g] in tetrahydrofuran (40 ml) was added with stirring at 0° C. The reaction was refluxed for 3 hours, cooled to 0° C., water (3 ml) was added dropwise followed by 15% sodium hydroxide (3 ml) and a further portion of water (9 ml). The suspension was filtered through solka-flok and the solvent removed under reduced pressure. Dichloromethane (50 ml) was added, the organic phase washed with brine (25 ml) dried over magnesium sulphate and the solvent removed under reduced pressure yielding the title compound as a white foam 5.4 g (67%).

Workup

temperatureThe reaction was refluxed for 3 hours
temperaturecooled to 0° C.
filtrationThe suspension was filtered through solka-flok and the solvent
customremoved under reduced pressure
additionDichloromethane (50 ml) was added
washthe organic phase washed with brine (25 ml)
dry with materialdried over magnesium sulphate
customthe solvent removed under reduced pressure

Sources & evidence

ORD record: ord-69b82512971c44f685a7bca09bba6dcf
Source dataset: uspto-grants-1991_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04992447

Reaction notes

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