Hydrochloric Acid → HCID 23136406, compound

HRID 2422227Notes

Reaction equation

HRID 2422227 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 mixture was stirred overnight at room temperature. 1N Hydrochloric acid (20 mL) was added and the mixture was stirred for 20 min. The mixture was 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 by silica gel column chromatography (hexane/ethyl acetate=10:1) to give the title compound. yield 60%, oil.

Workup

  1. stirringthe mixture was stirred for 20 min
  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 by silica gel column chromatography (hexane/ethyl acetate=10:1)

Sources & evidence

ORD record
ord-84939383131f48c68097a4310bc3e49c
Source dataset
uspto-grants-2011_06
Patent number
US07960369B2

Reaction notes

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