Potassium Carbonate → HCID 66707351, compound

HRID 1496932Notes

Reaction equation

HRID 1496932 reaction equation
[F:1][C:2]([F:13])([F:12])[O:3][C:4]1[CH:11]=[CH:10][C:7]([CH:8]=O)=[CH:6][CH:5]=1.C([O-])([O-])=O.[K+].[K+].[Br-].[CH3:21][O:22][C:23]([C:25]1[CH:50]=[CH:49][C:28]([CH2:29][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=[CH:27][CH:26]=1)=[O:24]>C1COCC1.C(Cl)Cl.C1OCCOCCOCCOCCOCCOC1>[F:1][C:2]([F:13])([F:12])[O:3][C:4]1[CH:11]=[CH:10][C:7](/[CH:8]=[CH:29]/[C:28]2[CH:49]=[CH:50][C:25]([C:23]([O:22][CH3:21])=[O:24])=[CH:26][CH:27]=2)=[CH:6][CH:5]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 69573p-(Trifluoromethoxy)benzaldehydeHCID 2764257[4-(Methoxycarbonyl)benzyl](triphenyl)phosphonium bromide

Product 1

HCID 66707351HCID 66707351, compoundYield 42%

Reagents, catalysts & solvents 3

HCID 2855718-Crown-6CatalystHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

4-(Trifluoromethoxy)benzaldehyde (125) (0.928 g, 4.88 mmol), K2CO3 (2.8 g, 20 mmol) and 18-crown-6 (0.04 g, 0.15 mmol) were added to a solution of [4-(methoxycarbonyl)benzyl]triphenylphosphonium bromide (124) (2.00 g, 4.07 mmol) in THF (60 mL) and CH2Cl2 (40 mL). The mixture was refluxed under N2 for 18 h, and then partitioned between EtOAc and water. The organic layer was washed with brine and the solvent was removed. Column chromatography of the residue on silica gel, eluting with 19:1 hexanes:EtOAc, gave a crude product which was recrystallised from hexanes to give methyl 4-{(E)-2-[4-(trifluoromethoxy)phenyl]ethenyl}benzoate (126) (0.549 g, 42%) as white flakes: mp (hexanes) 120-122° C.; NMR (CDCl3) δ 8.03 (d, J=8.4 Hz, 2H), 7.51-7.58 (m, 4H), 7.16-7.24 (m, 3H), 7.09 (d, J=16.3 Hz, 1H), 3.93 (s, 3H). APCI MS m/z 323 [M+H]+.

Workup

  1. temperatureThe mixture was refluxed under N2 for 18 h
  2. custompartitioned between EtOAc and water
  3. washThe organic layer was washed with brine
  4. customthe solvent was removed
  5. washColumn chromatography of the residue on silica gel, eluting with 19:1 hexanes
  6. customEtOAc, gave a crude product which
  7. customwas recrystallised from hexanes

Sources & evidence

ORD record
ord-8106f6bee4fb48a9a917b62302df27d3
Source dataset
uspto-grants-2015_12
Patent number
US09198913B2

Reaction notes

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