Tetrahydrofuran → HCID 67147047, compound

HRID 2422214Notes

Reaction equation

HRID 2422214 reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH:2]1[O:10][C:11]1[CH:16]=[CH:15][C:14](/[CH:17]=[CH:18]/[C:19]([O:21][CH3:22])=[O:20])=[CH:13][CH:12]=1.O1CCCC1>[C].[Pd].CO>[CH2:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[CH2:1][CH:2]1[O:10][C:11]1[CH:16]=[CH:15][C:14]([CH2:17][CH2:18][C:19]([O:21][CH3:22])=[O:20])=[CH:13][CH:12]=1

Participants

5

Reactant 2

HCID 8028TetrahydrofuranHCID 67145671HCID 67145671, compound

Product 1

HCID 67147047HCID 67147047, compoundYield 110.3%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

A mixture of methyl (E)-3-[4-[(2,3-dihydro-1H-inden-2-yl)oxy]phenyl]-2-propenoate (0.76 g, 2.6 mmol), tetrahydrofuran (10 mL), methanol (5 mL) and 10% palladium carbon (50% water-containing product, 0.10 g) was stirred overnight at room temperature under a hydrogen atmosphere. The reaction mixture was filtered and concentrated. Water was added, and the mixture was extracted with ethyl acetate. The extract was washed with water, dried over anhydrous magnesium sulfate and concentrated. The residue was recrystallized from ethyl acetate-methanol to give the title compound (0.85 g, yield 89%).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated
  3. additionWater was added
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe extract was washed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated
  8. customThe residue was recrystallized from ethyl acetate-methanol

Sources & evidence

ORD record
ord-70c86ef347f54c7baffae9db99246722
Source dataset
uspto-grants-2011_06
Patent number
US07960369B2

Reaction notes

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