Pyridine → HCID 54190065, compound

HRID 1378295Notes

Reaction equation

HRID 1378295 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([O:14][CH2:15][CH3:16])(OCC)[CH2:9][CH3:10])=[CH:4][CH:3]=1.N1C=CC=CC=1.[O:23](C(C(F)(F)F)=O)[C:24]([C:26]([F:29])([F:28])[F:27])=O>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([O:14][CH2:15][CH3:16])=[C:9]([CH3:10])[C:24](=[O:23])[C:26]([F:29])([F:28])[F:27])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 9845Trifluoroacetic anhydrideHCID 22906421HCID 22906421, compound

Product 1

HCID 54190065HCID 54190065, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Conditions

Temperature
0 °C

Procedure

A solution of 2.0 g of 1-chloro-4-(1,1-diethoxypropyl)benzene and 2.5 mL of CH2Cl2 was treated with 1.45 mL of pyridine. The solution was cooled to 0° C. and treated with 5.5 mL of (CF3CO)2O in 2.5 mL of CH2Cl2. After heating overnight at reflux, the reaction mixture was cooled, diluted with CH2Cl2 and 12 mL of ice cold water was added. The organic layer was seperated and washed with 20 mL of 1N HCl, followed by a washing with 20 mL of 10% Na2CO3 and two washing with 20 mL of water. The organic layer was dried over Na2SO4 and concd in vacuo to yield 1.69 g of a dark brown oil. Chromatographic purification (silica, 10% ethyl acetate in hexanes) yielded 1.0 g of a yellow oil. Bulb to bulb distillation gave 0.45 g of a very pure light yellow oil: μ(23,D) 1.5137; major geometric isomer: 1HNMR (CDCl3) δ 1.22 (t, 3H, 7.0 Hz), 1.70 (s, 3H), 3.64 (q, 2H, 7.0 Hz), 7.30 (d, 2H, 8.3 Hz), 7.46 (d, 2H, 8.4 Hz). 19FNMR (CDCl3) δ -74.68 (CF3). Anal. Calcd for C13H12O2F3Cl: C, 53.35; H, 4.13. Found: C, 53.44; H, 4.10.

Workup

  1. temperatureAfter heating overnight
  2. temperatureat reflux
  3. temperaturethe reaction mixture was cooled
  4. additionwas added
  5. customThe organic layer was seperated
  6. washwashed with 20 mL of 1N HCl
  7. dry with materialThe organic layer was dried over Na2SO4 and concd in vacuo

Sources & evidence

ORD record
ord-eb9cbd4fbf5245bcb0eb34ff7cd057c5
Source dataset
uspto-grants-1997_09
Patent number
US05668088

Reaction notes

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