Triethylamine → Methyl 4,4-difluoro-3-oxo-2-(morpholin-4-ylmethylidene)butyrate

HRID 1879284Notes

Reaction equation

[N:1]1([CH:7]=[CH:8][C:9]([O:11][CH3:12])=[O:10])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.C(N(CC)CC)C.[F:20][CH:21]([F:25])[C:22](F)=[O:23]>C1(C)C=CC=CC=1>[F:20][CH:21]([F:25])[C:22](=[O:23])[C:8](=[CH:7][N:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1)[C:9]([O:11][CH3:12])=[O:10]

Participants

Conditions

Temperature: -30 °C

Procedure

Methyl 3-morpholin-4-ylacrylate (96.3%, 8.5 g, 50 mmol) and triethylamine (5.2 g, 50 mmol) were initially charged in toluene (250 ml) and cooled to −30° C. At this temperature, difluoroacetyl fluoride (5.0 g, 50 mmol) was introduced. The reaction mixture was stirred at −30° C. for 3 h and then, over a period of 1 hour, warmed to room temperature. Under reduced pressure, the reaction mixture was freed from the solvent. The residue obtained was 15.5 g of an orange solid which, according to quant. 1H-NMR, consisted to 66.4% of methyl 4,4-difluoro-3-oxo-2-(morpholin-4-ylmethylidene)butyrate (yield: 82%). 1H-NMR (CDCl3): δ=3.4 (m, 2H), 3.7 (m, 2H), 3.75 (s, 3H), 3.85 (m, 2H), 6.6 (t, 1H), 7.85 ppm (s, 1H).

Workup

waitover a period of 1 hour
temperaturewarmed to room temperature
customThe residue obtained

Sources & evidence

ORD record: ord-235367e7de9c4f178740b1f9c68a1673
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08314233B2

Reaction notes

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