Aluminium lithium hydride → HCID 22477758, compound

HRID 2182342Notes

Reaction equation

[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([N:14]1[C:18]([C:19](OC)=[O:20])=[CH:17][C:16]([O:23][CH2:24][CH3:25])=[N:15]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>O1CCCC1>[CH2:7]([N:14]1[C:18]([CH2:19][OH:20])=[CH:17][C:16]([O:23][CH2:24][CH3:25])=[N:15]1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

Conditions

Temperature: 0 °C

Procedure

11.1 mg of lithium aluminium hydride are added to a solution of 76 mg of methyl 2-benzyl-5-ethoxy-2H-pyrazole-3-carboxylate in 0.75 ml of tetrahydrofuran, cooled to a temperature in the region of 0° C. by an ice bath. After 3 hours at a temperature in the region of 0° C., 22.2 mg of lithium aluminium hydride are added and the reaction medium is allowed to warm to a temperature in the region of 20° C. After 30 minutes at a temperature in the region of 20° C., 10 ml of ice-cold water are added and the reaction mixture is then filtered through Celite. After separation of the phases by settling, the aqueous phase is extracted with ethyl acetate. The organic phases are combined, dried over magnesium sulphate and concentrated under reduced pressure. 45.7 mg of (2-benzyl-5-ethoxy-2H-pyrazol-3-yl)methanol are thus obtained in the form of a brown lacquer, the characteristics of which are as follows:

Workup

temperatureto warm to a temperature in the region of 20° C
filtrationthe reaction mixture is then filtered through Celite
customAfter separation of the phases
extractionthe aqueous phase is extracted with ethyl acetate
dry with materialdried over magnesium sulphate
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-13786951334b407f800e073d5fdbe4f9
Source dataset: uspto-grants-2005_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06897208B2

Reaction notes

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