Diethyl Ether → 4-(p-Chlorophenyl)-4-methyl-2-pentenal

HRID 610849Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:15])([CH3:14])[C:9](F)=[CH:10][C:11]#N)=[CH:4][CH:3]=1.[H-].C([Al+]CC(C)C)C(C)C.C([O:28]CC)C>CCCCCC.O.Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:15])([CH3:14])[CH:9]=[CH:10][CH:11]=[O:28])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: -40 °C

Procedure

A solution of 4-(p-chlorophenyl)-3-fluoro-4-methyl-2-pentenenitrile, (Z)- (15.6 g, 69.7 mmol) in diethyl ether is treated dropwise with diisobutylaluminum hydride (83.6 mmol, 83.6 mL of a 1M solution in hexane) over 90 minutes at -45° C. under nitrogen, stirred at -40° C. for 35 minutes, and diluted sequentially with water and 2N hydrochloric acid at -10° C. The resultant aqueous mixture is stirred at room temperature for one hour and extracted with diethyl ether. The organic extracts are combined, washed sequentially with water, 2N hydrochloric acid and water, dried over anhydrous sodium sulfate, and concentrated in vacuo to give the title product as a brown oil (15.34 g, 97% yield).

Workup

stirringThe resultant aqueous mixture is stirred at room temperature for one hour
extractionextracted with diethyl ether
washwashed sequentially with water, 2N hydrochloric acid and water
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-f6e435d6224c4651ad1c500264928ec7
Source dataset: uspto-grants-1999_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05998673

Reaction notes

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