Propane, 2,2-diethoxy- → HCID 54098869, compound

HRID 1681307Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:9](=[N:17][OH:18])[CH2:10][C:11]1[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=1.[CH2:19]([O:21][C:22](OCC)([CH3:24])[CH3:23])[CH3:20]>C1(C)C(C)=CC=CC=1>[CH2:19]([O:21][C:22]([O:18][N:17]=[C:9]([C:3]1[C:4]([F:8])=[CH:5][CH:6]=[CH:7][C:2]=1[F:1])[CH2:10][C:11]1[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=1)([CH3:24])[CH3:23])[CH3:20]

Participants

Conditions

Temperature: 80 °C

Procedure

A solution of 7.45 g of 2',6'-difluoro-2-(3-pyridyl)acetophenone oxime in 170 ml of xylene is mixed with 8.00 g of diethoxypropane and then heated to 80° C. with stirring. After a clear solution has formed, 0.20 g of pulverised Amberlyst® A15 is added and the entire mixture is heated to reflux temperature. After 6 hours, the reaction mixture is subjected to clarifying filtration through Celite® and the filtrate is freed of excess solvent at 60° C. in a water jet vacuum. After drying in a high vacuum, 2',6'-difluoro-2-(3-pyridyl)acetophenone O-(1-ethoxy-1-methylethyl)oxime is obtained as an E/Z isomer mixture in the form of a yellow oil. On chromatographic separation on silica gel using n-hexane/ethyl acetate (3:1), the E isomer [1H-NMR (CDCl3, 200 MHz): 1.428 ppm (s, --C(CH3)2)] is obtained first in the form of slightly yellowish oils.

Workup

customAfter a clear solution has formed
addition0.20 g of pulverised Amberlyst® A15 is added
temperaturethe entire mixture is heated
temperatureto reflux temperature
filtrationfiltration through Celite®
customis freed of excess solvent at 60° C. in a water jet vacuum
customAfter drying in a high vacuum

Sources & evidence

ORD record: ord-e9bee6170b084dc08b2e84726cb44bdd
Source dataset: uspto-grants-1992_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05171354

Reaction notes

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