Trifluoroacetic acid → HCID 18319554, compound

HRID 1699387Notes

Reaction equation

HRID 1699387 reaction equation
I[C:2]1[C:12]2[O:11][CH2:10][CH2:9][C:8]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:7][C:6]=2[CH:5]=[CH:4][CH:3]=1.[F:18][C:19]([F:24])([F:23])C(O)=O.[Na]>CN1CCCC1=O.[Cu]I>[F:18][C:19]([F:24])([F:23])[C:2]1[C:12]2[O:11][CH2:10][CH2:9][C:8]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:7][C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 5360545SodiumHCID 18319552HCID 18319552, compound

Product 1

HCID 18319554HCID 18319554, compound

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
160 °C

Procedure

A mixture of ethyl 2,3-dihydro-9-iodo-1-benzoxepin-4-carboxylate (1.00 g), trifluoroacetic acid, sodium salt (1.58 g), and copper(I) iodide (1.11 g) in 1-methyl-2-pyrrolidinone (10 ml) was stirred at 160° C. under nitrogen atmosphere for 6 hours and partitioned between ethyl acetate and 1N hydrochloric acid. The aqueous layer was extracted twice with ethyl acetate. The combined organic layer was washed successively with saturated aqueous sodium bicarbonate and brine, dried over anhydrous magnesium sulfate, and evaporated in vacuo. The residue was purified by column chromatography on silica gel using a mixture of n-hexane and ethyl acetate (4:1) to give ethyl 2,3-dihydro-9-trifluoromethyl-1-benzoxepin-4-carboxylate (0.93 g).

Workup

  1. custompartitioned between ethyl acetate and 1N hydrochloric acid
  2. extractionThe aqueous layer was extracted twice with ethyl acetate
  3. washThe combined organic layer was washed successively with saturated aqueous sodium bicarbonate and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customevaporated in vacuo
  6. customThe residue was purified by column chromatography on silica gel using
  7. additiona mixture of n-hexane and ethyl acetate (4:1)

Sources & evidence

ORD record
ord-966bf1ceaada4bbba6743429b9100494
Source dataset
uspto-grants-2002_02
Patent number
US06346527B1

Reaction notes

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