HCID 86623633, compound → Methyl (5-methoxy-2,3-dihydro-1H-inden-1-yl)acetate

HRID 1821054Notes

Reaction equation

HRID 1821054 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][CH3:16])=[O:14])/[CH2:7][CH2:6]2>CO.[Pd]>[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][CH3:16])=[O:14])[CH2:7][CH2:6]2

Participants

4

Reactant 1

HCID 86623633HCID 86623633, compound

Product 1

HCID 71710973Methyl (5-methoxy-2,3-dihydro-1H-inden-1-yl)acetateYield 99.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a mixture of 10% Pd—C (200 mg) in methanol (10 mL) under an atmosphere of nitrogen, methyl (2E)-(5-methoxy-2,3-dihydro-1H-inden-1-ylidene)acetate (2.00 g, 9.16 mmol, from Step A) was added as a solid. The mixture was evacuated and filled with 1 atmosphere of H2. After 1 hr, the mixture was filtered through a pad of Celite® and the filtrate concentrated in vacuo. The residue was azeotroped with toluene to afford 2.00 g of the title compound: 1H NMR (CDCl3) δ 1.78-1.84 (m, 1H), 2.40-2.50 (m, 2H), 2.79 (dd, 1H, J=5.7, 15.3 Hz), 2.87-2.98 (m, 2H), 3.57-3.60 (m, 1H), 3.77 (s, 3H), 3.83 (s, 3H), 6.77 (dd, 1H, J=2.3, 8.2 Hz), 6.83 (d, 1H, J=1.9 Hz), 7.12 (d, 1H, J=8.2 Hz).

Workup

  1. customThe mixture was evacuated
  2. additionfilled with 1 atmosphere of H2
  3. filtrationthe mixture was filtered through a pad of Celite®
  4. concentrationthe filtrate concentrated in vacuo
  5. customThe residue was azeotroped with toluene

Sources & evidence

ORD record
ord-82f657106bba43b3aadae5803c67a65e
Source dataset
uspto-grants-2009_10
Patent number
US07605171B2

Reaction notes

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