Hydrochloric Acid → HCID 67047753, compound

HRID 2112609Notes

Reaction equation

HRID 2112609 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. 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
  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-2caa476380354081b6688b12994dd4d4
Source dataset
uspto-grants-2009_04
Patent number
US07524849B2

Reaction notes

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