Acetic acid, 2-(triphenylphosphoranylidene)-, methyl ester → 3-(2-Propyl-4-trifluoromethyl-phenyl)-acrylic acid methyl ester

HRID 1042469Notes

Reaction equation

[CH2:1]([C:4]1[CH:11]=[C:10]([C:12]([F:15])([F:14])[F:13])[CH:9]=[CH:8][C:5]=1[CH:6]=O)[CH2:2][CH3:3].C1(P(=[CH:35][C:36]([O:38][CH3:39])=[O:37])(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1(C)C=CC=CC=1.CCOC(C)=O>[CH3:39][O:38][C:36](=[O:37])[CH:35]=[CH:6][C:5]1[CH:8]=[CH:9][C:10]([C:12]([F:15])([F:14])[F:13])=[CH:11][C:4]=1[CH2:1][CH2:2][CH3:3]

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of the aldehyde obtained above in toluene was added methyl (triphenylphosphoranylidene)acetate (285 mg, 0.85 mmol), and the resulting mixture was heated at 80° C. for 3 hrs. The reaction mixture was diluted with EtOAc, and washed with water and brine. The organic layer was dried over anhydrous MgSO4 and concentrated under reduced pressure. The resulting residue was purified by column chromatography (Hex/EtOAc=4/1) to give the title compound (220 mg, 96%).

Workup

washwashed with water and brine
dry with materialThe organic layer was dried over anhydrous MgSO4
concentrationconcentrated under reduced pressure
customThe resulting residue was purified by column chromatography (Hex/EtOAc=4/1)

Sources & evidence

ORD record: ord-ab74fa64694644068e6188e1e86daa14
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08557872B2

Reaction notes

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