Ethyl (5-methoxy-2,3-dihydro-1H-inden-1-ylidene)ethanoate → HCID 10263432, compound

HRID 2177388Notes

Reaction equation

HRID 2177388 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[C:8](=[CH:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH2:7][CH2:6]2.[H][H]>[C].[Pd].CO>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[CH:8]([CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH2:7][CH2:6]2

Participants

5

Reactant 2

HCID 53401862Ethyl (5-methoxy-2,3-dihydro-1H-inden-1-ylidene)ethanoateHCID 178418361HCID 178418361, compound

Product 1

HCID 10263432HCID 10263432, compound

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

Into a 50-mL round-bottom flask, was placed ethyl 2-(5-methoxy-2,3-dihydro-1H-inden-1-ylidene)acetate (500 mg, 2.15 mmol, 1.00 equiv), methanol (3 mL), Palladium carbon (500 mg). To the mixture hydrogen was introduced in. The resulting solution was stirred overnight at room temperature. The solids were filtered out. The mixture was dried over anhydrous sodium sulfate. The solids were filtered out. The resulting mixture was concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (15:85). This resulted in 300 mg (59%) of ethyl 2-(5-methoxy-2,3-dihydro-1H-inden-1-yl)acetate as colorless oil.

Workup

  1. customInto a 50-mL round-bottom flask, was placed
  2. filtrationThe solids were filtered out
  3. dry with materialThe mixture was dried over anhydrous sodium sulfate
  4. filtrationThe solids were filtered out
  5. concentrationThe resulting mixture was concentrated under vacuum
  6. customThis resulted in 300 mg (59%) of ethyl 2-(5-methoxy-2,3-dihydro-1H-inden-1-yl)acetate as colorless oil

Sources & evidence

ORD record
ord-11ac98084310431987f810af8fa39692
Source dataset
uspto-grants-2015_06
Patent number
US09067898B1

Reaction notes

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