HCID 18617215, compound → HCID 18617217, compound

HRID 1263562Notes

Reaction equation

HRID 1263562 reaction equation
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[CH2:12][CH2:13]/[CH:14]=[CH:15]/[C:16]1[CH:28]=[CH:27][C:19]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])=[CH:18][CH:17]=1>C1COCC1.CCO.[Pd]>[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[CH2:12][CH2:13][CH2:14][CH2:15][C:16]1[CH:17]=[CH:18][C:19]([C:20]([O:22][C:23]([CH3:24])([CH3:25])[CH3:26])=[O:21])=[CH:27][CH:28]=1

Participants

4

Reactant 1

HCID 18617215HCID 18617215, compound

Product 1

HCID 18617217HCID 18617217, compoundYield 100.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

tert-Butyl 4-[(E)-4-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-1-butenyl]benzoate (15.1 g) was dissolved in 1:1 THF/EtOH (150 mL). 10% Pd on carbon (6.0 g) was added and the reaction placed on a Parr hydrogenator under 50 psi of H2. The reaction was shaken for 6 h. The reaction was filtered through a pad of celite and the celite washed with ethanol (3×100 mL). The organic extracts were concentrated to afford 15.3 g of tert-butyl 4-[4-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)butyl]benzoate: 1H NMR (CDCl3, 400 MHz) 7.88 (d, 2H, J=8.1 Hz), 7.82 (dd, 2H, J=3.0, 3.1 Hz), 7.77 (dd, 2H, J=3.0, 3.2 Hz), 7.2 (d, 2H, J=8.1 Hz), 3.7 (t, 2 h, J=6.9 Hz), 2.7 (t, 2H, J=6.9 Hz), 1.7 (m, 4H), 1.60 (s, 9H).

Workup

  1. filtrationThe reaction was filtered through a pad of celite
  2. washthe celite washed with ethanol (3×100 mL)
  3. concentrationThe organic extracts were concentrated

Sources & evidence

ORD record
ord-27290c0c9bc44cefbb08aecaa22bd3ed
Source dataset
uspto-grants-2003_04
Patent number
US06541492B1

Reaction notes

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