Hydrochloric Acid → HCID 23136406, compound

HRID 1678570Notes

Reaction equation

HRID 1678570 reaction equation
[CH:1]1([O:10][C:11]2[C:16]([F:17])=[CH:15][C:14](/[CH:18]=[CH:19]/[C:20]([O:22][CH3:23])=[O:21])=[CH:13][C:12]=2[F:24])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.[Sm].II.Cl>O.CO.O1CCCC1>[CH:1]1([O:10][C:11]2[C:12]([F:24])=[CH:13][C:14]([CH2:18][CH2:19][C:20]([O:22][CH3:23])=[O:21])=[CH:15][C:16]=2[F:17])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 807IodineHCID 23951SamariumHCID 67145905HCID 67145905, compound

Product 1

HCID 23136406HCID 23136406, compoundYield 60%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of methyl (E)-3-[4-[(2,3-dihydro-1H-inden-1-yl)oxy]-3,5-difluorophenyl]-2-propenoate (0.52 g, 1.6 mmol), samarium (1.2 g, 7.9 mmol), tetrahydrofuran (3 mL) and methanol (7 mL) was added iodine (0.80 g, 3.2 mmol), and the reaction mixture was stirred at room temperature overnight. 1 N Hydrochloric acid (20 mL) was added thereto, and the mixture was stirred for 20 minutes, then diluted with water and extracted with ethyl acetate. The extract was washed with water, dried over anhydrous sodium sulfate and concentrated. The residue was purified with silica gel column chromatography (hexane/ethyl acetate=10:1) to give the title compound. Yield 60%.

Workup

  1. stirringthe mixture was stirred for 20 minutes
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified with silica gel column chromatography (hexane/ethyl acetate=10:1)

Sources & evidence

ORD record
ord-1325dfc932b245cab9133082dd945a66
Source dataset
uspto-grants-2011_08
Patent number
US08008525B2

Reaction notes

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