HCID 131733004, compound → HCID 118184909, compound

HRID 2177401Notes

Reaction equation

HRID 2177401 reaction equation
C([O:8][C:9]1[CH:10]=[CH:11][C:12](/[CH:19]=[CH:20]/[C:21]([O:23][CH2:24][CH3:25])=[O:22])=[C:13]2[C:17]=1[C:16](=[O:18])[CH2:15][CH2:14]2)C1C=CC=CC=1.[H][H]>[Pd].C(OCC)(=O)C>[OH:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:19][CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])=[C:13]2[C:17]=1[C:16](=[O:18])[CH2:15][CH2:14]2

Participants

5

Reactant 2

HCID 131733004HCID 131733004, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 118184909HCID 118184909, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
15 °C

Procedure

Into a 50-mL round-bottom flask was placed ethyl (2E)-3-[7-(benzyloxy)-1-oxo-2,3-dihydro-1H-inden-4-yl]prop-2-enoate (500 mg, 1.49 mmol, 1.00 equiv), ethyl acetate (10 mL), Palladium on carbon (250 mg), and hydrogen was introduced last. The resulting solution was stirred overnight at 15° C. The reaction progress was monitored by LCMS. The solids were removed by filtration, the filtrate dried over anhydrous sodium sulfate, and concentrated under reduced pressure. This resulted in 350 mg (90%) of ethyl 3-(7-hydroxy-1-oxo-2,3-dihydro-1H-inden-4-yl)propanoate as a light yellow solid. Mass spectrum (ESI, m/z): Calcd. for C14H16O4, 247.1 (M−H). found 247.1.

Workup

  1. customInto a 50-mL round-bottom flask was placed
  2. customThe solids were removed by filtration
  3. dry with materialthe filtrate dried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThis resulted in 350 mg (90%) of ethyl 3-(7-hydroxy-1-oxo-2,3-dihydro-1H-inden-4-yl)propanoate as a light yellow solid

Sources & evidence

ORD record
ord-cfe2856ae17949138c0f74c8beb5bee0
Source dataset
uspto-grants-2015_06
Patent number
US09067898B1

Reaction notes

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