HCID 13989886, compound → HCID 22285910, compound

HRID 1698929Notes

Reaction equation

HRID 1698929 reaction equation
C1(C[O:8][CH2:9][CH2:10][CH2:11][O:12][N:13]2[C:21](=[O:22])[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:14]2=[O:23])C=CC=CC=1.[H][H]>C(O)C.[Pd]>[OH:8][CH2:9][CH2:10][CH2:11][O:12][N:13]1[C:21](=[O:22])[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:14]1=[O:23]

Participants

5

Reactant 2

HCID 13989886HCID 13989886, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 22285910HCID 22285910, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 8.2 g (27 mmol) of 2-[3-(phenylmethoxy)propoxy]isoindoline-1,3-dione, as prepared in the preceding step, in 120 mL anhydrous ethanol under nitrogen was added 1.5 g of 10 wt % Pd/C. Then the nitrogen in the reaction was replaced with hydrogen and the reaction was stirred at room temperature for 5 h. After the reaction was completed, the mixture was filtered through a pad of Celite (diatomaceous earth). The solvent of the filtrate was removed under reduced pressure. The residue was chromatographed on a silica gel column using ethyl acetate/hexanes (1:1, v/v) as eluent to yield 4.4 g (75%) of white solid as product: 1H NMR (300 MHz, CDCl3) δ7.85-7.81 (m, 2H), 7.78-7.74 (m, 2H), 4.37 (t, J=5.88 Hz, 2H), 3.93 (t, J=5.80 Hz, 2H), 2.55 (br s, 1H), 1.99 (quintet, J=5.86, 2H).

Workup

  1. filtrationthe mixture was filtered through a pad of Celite (diatomaceous earth)
  2. customThe solvent of the filtrate was removed under reduced pressure
  3. customThe residue was chromatographed on a silica gel column

Sources & evidence

ORD record
ord-a53a6918da354c58bbe90dc79c5c1d5d
Source dataset
uspto-grants-2002_02
Patent number
US06344484B1

Reaction notes

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