Ethyl Acetoacetate → HCID 86743386, compound

HRID 1607897Notes

Reaction equation

[C:1]([O:7][CH2:8][CH3:9])(=[O:6])[CH2:2][C:3]([CH3:5])=[O:4].[H-].[Na+].C([Li])CCC.[F:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]2[C:29](/[CH:30]=[CH:31]/[CH:32]=[O:33])=[C:28]([CH3:34])[N:27]=[C:26]([CH3:35])[N:25]=2)=[CH:20][CH:19]=1>O1CCCC1>[F:17][C:18]1[CH:19]=[CH:20][C:21]([C:24]2[C:29]([CH:30]=[CH:31][CH:32]([OH:33])[CH2:5][C:3](=[O:4])[CH2:2][C:1]([O:7][CH2:8][CH3:9])=[O:6])=[C:28]([CH3:34])[N:27]=[C:26]([CH3:35])[N:25]=2)=[CH:22][CH:23]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of ethyl acetoacetate (11.65 mL, 0.0914 mol) in 50 mL of anhydrous tetrahydrofuran was added dropwise with stirring to a suspensionof sodium hydride (2.39 g, 0.0992 mol) in anhydrous tetrahydrofuran at 0° C. under nitrogen. The resulting mixture was stirred at 0° C. for ten minutes, after which n-butyl lithium (38.1 mL, 2.4M solution in tetrahydrofuran, 0.0914 mol) was added dropwise. The resultingorange solution was stirred for an additional ten minutes and then cooled to -78° C. A solution of (E)-3-[4-(4-fluorophenyl)-2,6-dimethyl-5-pyrimidinyl]-2-propenal (21.27 g,0.083 mol) in 100 mL of anhydrous tetrahydrofuran was added dropwise. The resulting solution was stirred for thirty minutes, and the cooling bath was removed, after which the reaction was quenched by the addition of 12 mL of glacial acetic acid.

Workup

stirringThe resultingorange solution was stirred for an additional ten minutes
temperaturecooled to -78° C
stirringThe resulting solution was stirred for thirty minutes
customthe cooling bath was removed
customafter which the reaction was quenched by the addition of 12 mL of glacial acetic acid

Sources & evidence

ORD record: ord-c11e387e726a42648fbbb183825c49f2
Source dataset: uspto-grants-1989_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04868185

Reaction notes

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