Acrolein → HCID 59780172, compound

HRID 1359900Notes

Reaction equation

[CH3:1][N:2]1[CH:6]=[C:5]([C:7]([NH:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[O:8])[C:4]([C:16]([F:19])([F:18])[F:17])=[N:3]1.C([N-]C(C)C)(C)C.[Li+].[CH:28]([CH:30]=[CH2:31])=[O:29].[NH4+].[Cl-]>C1COCC1>[OH:29][CH:28]([CH:30]=[CH2:31])[CH:10]([NH:9][C:7]([C:5]1[C:4]([C:16]([F:18])([F:17])[F:19])=[N:3][N:2]([CH3:1])[CH:6]=1)=[O:8])[C:11]([O:13][CH2:14][CH3:15])=[O:12]

Participants

Conditions

Temperature: -50 °C

Procedure

At −50° C., 3.45 g (12.4 mmol) of ethyl [(1-methyl-3-trifluoromethyl-1H-pyrazole-4-carbonyl)amino]acetate dissolved in THF were added dropwise to 18.5 ml (37.0 mmol) of a 2M solution of lithium diisopropylamide in THF/heptanelethylbenzene. After 1.5 h of stirring at −50° C., the mixture was cooled to −78° C. and 0.83 g (14.8 mmol) of acrolein dissolved in THF were added dropwise. After 2 h of stirring at −78° C., the mixture was hydrolyzed with sat. NH4Cl solution and warmed to RT. After separation of the phases, the organic phase was dried and the solvent was removed. The residue was purified chromatographically (SiO2, cyclohexane/ethyl acetate). This gave 1.65 g (40% of theory) of the title compound as a colorless solid (about 1:1 diastereomer mixture) which was used without further purification.

Workup

temperaturethe mixture was cooled to −78° C.
additionwere added dropwise
stirringAfter 2 h of stirring at −78° C.
temperaturewarmed to RT
customAfter separation of the phases
customthe organic phase was dried
customthe solvent was removed
customThe residue was purified chromatographically (SiO2, cyclohexane/ethyl acetate)
customThis gave 1.65 g (40% of theory) of the title compound as a colorless solid (about 1:1 diastereomer mixture) which was used without further purification

Sources & evidence

ORD record: ord-04f2ae0c14fd40d294ee03426aba6ea2
Source dataset: uspto-grants-2011_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07879761B2

Reaction notes

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