Hydrochloric Acid → HCID 68713615, compound

HRID 1911569Notes

Reaction equation

HRID 1911569 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([OH:11])=[O:10])[CH:5]=[CH:6][CH:7]=1.C([N-]C(C)C)(C)C.[Li+].I[CH2:21][CH2:22][C:23]([F:26])([F:25])[F:24].Cl>O1CCCC1.O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]([CH2:21][CH2:22][C:23]([F:26])([F:25])[F:24])[C:9]([OH:11])=[O:10])[CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 158793-Chlorophenylacetic acidHCID 1561651,1,1-Trifluoro-3-iodopropaneHCID 2724682Lithium diisopropylamide

Product 1

HCID 68713615HCID 68713615, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of m-chlorophenylacetic acid (2.38 g, 14 mmol) in tetrahydrofuran (85 ml) was added at −78° C. lithium diisopropylamide solution (31 ml 1M in THF, 31 mmol). After stirring the mixture for 20 min 1-iodo-3,3,3-trifluoropropane (4.38 g, 20 mmol) was added and the mixture was allowed to warm to room temperature overnight. Water (5 ml) was added followed by 2N hydrochloric acid (10 ml). The reaction mixture was extracted twice with ethyl acetate. The combined organic layers were dried over MgSO4 and evaporated and the residue was purified by column chromatography (SiO2, heptane/EtOAc=9:1) to yield a colourless oil, (1.75 g, 47%); MS (EI): 264.9 (M+.).

Workup

  1. additionwas added
  2. extractionThe reaction mixture was extracted twice with ethyl acetate
  3. dry with materialThe combined organic layers were dried over MgSO4
  4. customevaporated
  5. customthe residue was purified by column chromatography (SiO2, heptane/EtOAc=9:1)
  6. customto yield a colourless oil, (1.75 g, 47%)

Sources & evidence

ORD record
ord-6aa30393007f47829991888e95ec4b8a
Source dataset
uspto-grants-2013_12
Patent number
US08604061B2

Reaction notes

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