Hydrochloric Acid → HCID 86639442, compound

HRID 1690222Notes

Reaction equation

HRID 1690222 reaction equation
[F:1][C:2]([F:31])([F:30])[C:3]([C:12]1[CH:17]=[CH:16][C:15]([O:18][C:19]2[CH:24]=[CH:23][C:22](I)=[C:21]([CH3:26])[CH:20]=2)=[C:14]([CH2:27][CH2:28][CH3:29])[CH:13]=1)([O:8][CH2:9][O:10][CH3:11])[C:4]([F:7])([F:6])[F:5].[CH2:32]([O:34]C=C[Sn](CCCC)(CCCC)CCCC)[CH3:33].Cl>C1(C)C=CC=CC=1>[CH3:26][C:21]1[CH:20]=[C:19]([O:18][C:15]2[CH:16]=[CH:17][C:12]([C:3]([O:8][CH2:9][O:10][CH3:11])([C:4]([F:7])([F:6])[F:5])[C:2]([F:31])([F:30])[F:1])=[CH:13][C:14]=2[CH2:27][CH2:28][CH3:29])[CH:24]=[CH:23][C:22]=1[C:32](=[O:34])[CH3:33]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 2763294(Z)-1-Ethoxy-2-(tributylstannyl)ethene2×HCID 86639420HCID 86639420, compound

Product 1

HCID 86639442HCID 86639442, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 4-(1,1,1,3,3,3-hexafluoro-2-(methoxymethoxy)propan-2-yl)-1-(4-iodo-3-methylphenoxy)-2-propylbenzene (393 mg, 0.699 mmol) in toluene (7.0 mL), ethoxyvinyltributyl tin (473 μL, 1.40 mmol) and tetrakis triphenylphosphine palladium (162 mg, 0.140 mmol) were added sequentially, and the resultant mixture was heated to reflux for 1 hour. Then, ethoxyvinyltributyl tin (946 μL, 2.80 mmol) was added and heated to reflux for 1.5 hours. After completion of the reaction, 5% aqueous solution of hydrochloric acid was added under ice-cold conditions, and the resultant mixture was stirred overnight. The reaction solution was filtered using celite and extracted with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium hydrogen carbonate and brine, and concentrated in vacuo. The obtained residue was purified using column chromatography (hexane/ethyl acetate), and 1-{2-methyl-4-[2-propyl-4-(2,2,2-trifluoro-1-methoxymethoxy-1-trifluoromethyl-ethyl)-phenoxy]-phenyl}-ethanone (291 mg, yield 80%) was obtained as a yellow oil.

Workup

  1. temperatureto reflux for 1 hour
  2. temperatureheated
  3. temperatureto reflux for 1.5 hours
  4. additionwas added under ice-cold conditions
  5. filtrationThe reaction solution was filtered
  6. extractionextracted with ethyl acetate
  7. washThe organic layer was washed with a saturated aqueous solution of sodium hydrogen carbonate and brine
  8. concentrationconcentrated in vacuo
  9. customThe obtained residue was purified

Sources & evidence

ORD record
ord-46af9b832fc14da189d60010bffb038a
Source dataset
uspto-grants-2012_04
Patent number
US08153634B2

Reaction notes

Loading…