HCID 58566745, compound → HCID 58566350, compound

HRID 2177203Notes

Reaction equation

HRID 2177203 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5](/[CH:11]=[CH:12]/[C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:6]2[C:10]=1[CH2:9][CH2:8][CH2:7]2.[H][H]>C(O)C.[Pd]>[OH:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:11][CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:6]2[C:10]=1[CH2:9][CH2:8][CH2:7]2

Participants

5

Reactant 2

HCID 58566745HCID 58566745, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 58566350HCID 58566350, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Conditions

Temperature
25 °C

Procedure

Into a 25-mL round-bottom flask, was placed a solution of ethyl (2E)-3-(7-hydroxy-2,3-dihydro-1H-inden-4-yl)prop-2-enoate (87.4 mg, 0.38 mmol, 1.00 equiv) in ethanol (4 mL) and palladium on carbon (80 mg). The mixture was then subject to an atmosphere of hydrogen and stirred for 12 h at 25° C. 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 (1:10). This resulted in 79.8 mg (91%) of ethyl 3-(7-hydroxy-2,3-dihydro-1H-inden-4-yl)propanoate as yellow oil.

Workup

  1. customInto a 25-mL round-bottom flask, was placed
  2. filtrationThe solids were filtered out
  3. concentrationThe resulting mixture was concentrated under vacuum
  4. customThis resulted in 79.8 mg (91%) of ethyl 3-(7-hydroxy-2,3-dihydro-1H-inden-4-yl)propanoate as yellow oil

Sources & evidence

ORD record
ord-e50bb380713841e58c9602a5de61d196
Source dataset
uspto-grants-2015_06
Patent number
US09067898B1

Reaction notes

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