Aluminium lithium hydride → HCID 57443264, compound

HRID 1689760Notes

Reaction equation

[H-].[H-].[H-].[H-].[Li+].[Al+3].C([O:9][C:10]([C:12]1[N:13]([C:20]2[C:25]([Cl:26])=[CH:24][CH:23]=[CH:22][C:21]=2[Cl:27])[N:14]=[CH:15][C:16]=1[CH:17]1[CH2:19][CH2:18]1)=O)C>C1COCC1>[CH:17]1([C:16]2[CH:15]=[N:14][N:13]([C:20]3[C:25]([Cl:26])=[CH:24][CH:23]=[CH:22][C:21]=3[Cl:27])[C:12]=2[CH2:10][OH:9])[CH2:19][CH2:18]1

Participants

Conditions

Temperature: 0 °C

Procedure

To a 0° C. mixture of LAH powder in THF (20 mL) is added a solution of 4-cyclopropyl-2-(2,6-dichloro-phenyl)-2H-pyrazole-3-carboxylic acid ethyl ester (2.4 mmol, 0.8 g) in THF (10 mL). The reaction is stirred for 2 h at 0° C. The reaction is quenched with a sequence of water (0.26 mL), 5N NaOH (0.26 mL) and water (0.78 mL). The reaction mixture is stirred for 1 h at 0° C. The reaction mixture is filtered and the filtrate is adsorbed onto silica gel and purified using a gradient of 30-50% EtOAc/Hexanes to yield the title compound (0.36 g, 53%). LC-ES/MS m/e 283.0 (M+1).

Workup

customThe reaction is quenched with a sequence of water (0.26 mL), 5N NaOH (0.26 mL) and water (0.78 mL)
stirringThe reaction mixture is stirred for 1 h at 0° C
filtrationThe reaction mixture is filtered
custompurified

Sources & evidence

ORD record: ord-1a83466f4d8744698a5ce6d677026c46
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08153624B2

Reaction notes

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