Hydrochloric Acid → HCID 67047753, compound

HRID 1786304Notes

Reaction equation

HRID 1786304 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[C:4]([F:9])[C:3]=1[CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12].C([N-]C(C)C)(C)C.[Li+].[CH:24]1([C:31](Cl)=[O:32])[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1.Cl>O1CCCC1>[CH:24]1([C:31](=[O:32])[CH:10]([C:3]2[C:2]([F:1])=[CH:7][C:6]([F:8])=[CH:5][C:4]=2[F:9])[C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 2724682Lithium diisopropylamideHCID 12556870Cycloheptanecarbonyl chlorideHCID 58980768HCID 58980768, compound

Product 1

HCID 67047753HCID 67047753, compoundYield 59.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of ethyl 2,4,6-trifluorophenylacetate (436 mg, 2.0 mmol) in 3 mL of tetrahydrofuran is cooled to −78° C., and lithium diisopropylamide (2.0 M in heptane/tetrahydrofuran/ethylbenzene, 1.0 mL, 2.0 mmol) is added dropwise with stirring. The mixture is stirred at −78° C. for 1 h, and cycloheptanecarboxylic acid chloride (321 mg, 2.0 mmol) is added dropwise. The mixture is warmed to room temperature and acidified with 2 mL of 1.0 N hydrochloric acid. The product is extracted with ethyl acetate. The organic layer is washed with saturated sodium chloride, dried over magnesium sulfate, and concentrated to a residue. The residue is chromatographed over silica gel, eluting with a gradient of hexanes to 10% ethyl acetate in hexanes. Concentration provides ethyl 3-cycloheptyl-3-oxo-2-(2,4,6-trifluorophenyl)propanoate as a colorless oil (410 mg). MS: m/z 341.2 (M−H).

Workup

  1. stirringThe mixture is stirred at −78° C. for 1 h
  2. extractionThe product is extracted with ethyl acetate
  3. washThe organic layer is washed with saturated sodium chloride
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated to a residue
  6. customThe residue is chromatographed over silica gel
  7. washeluting with a gradient of hexanes to 10% ethyl acetate in hexanes
  8. concentrationConcentration

Sources & evidence

ORD record
ord-782ec82f14a14050bce378ccea8104f8
Source dataset
uspto-grants-2009_03
Patent number
US07507739B2

Reaction notes

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