HCID 275729, compound → HCID 12646159, compound

HRID 431778Notes

Reaction equation

HRID 431778 reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][C:6]([CH:10]=[CH:11][C:12]([OH:14])=[O:13])=[CH:7][CH:8]=2)[CH2:3][CH2:2]1>C(O)C.[Pd]>[CH2:1]1[C:9]2[C:4](=[CH:5][C:6]([CH2:10][CH2:11][C:12]([OH:14])=[O:13])=[CH:7][CH:8]=2)[CH2:3][CH2:2]1

Participants

4

Reactant 1

HCID 275729HCID 275729, compound

Product 1

HCID 12646159HCID 12646159, compoundYield 110.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

3-(2,3-Dihydro-1H-inden-5-yl)-propenoic acid (500 mg, 2.66 mmol) (available from Aldrich) was taken up in ethanol (40 ml) and hydrogenated at 15 psi H2 pressure with 40 mg of 10% Pd/C for 4 h. The mixture was filtered through a short plug of Arbocel and the filtrate evaporated to give the title product (560 mg, approx. quantitative) which was used with no further purification; 1HNMR (400 MHz, CDCl3) δ: 1.98-2.07 (m, 2H), 2.75 (t, 2H), 2.80-2.90 (m, 6H), 6.95 (d, 1H), 7.03 (s, 1H), 7.08 (d, 1H); LRMS: m/z ES-189 (M−H).

Workup

  1. filtrationThe mixture was filtered through a short plug of Arbocel
  2. customthe filtrate evaporated

Sources & evidence

ORD record
ord-1341e85e9dd04a0fa8325233bdfa48d0
Source dataset
uspto-grants-2003_12
Patent number
US06660756B2

Reaction notes

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