HCID 17756178, compound → HCID 17755958, compound

HRID 2382553Notes

Reaction equation

HRID 2382553 reaction equation
[OH:1][CH2:2][CH2:3][C:4]#[C:5][C:6]1[CH:23]=[CH:22][C:9]([CH2:10][N:11]2[C:19](=[O:20])[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12]2=[O:21])=[CH:8][CH:7]=1.[H][H]>C(O)C.C(OCC)(=O)C.[Pd]>[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6]1[CH:7]=[CH:8][C:9]([CH2:10][N:11]2[C:19](=[O:20])[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12]2=[O:21])=[CH:22][CH:23]=1

Participants

5

Reactant 2

HCID 17756178HCID 17756178, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 17755958HCID 17755958, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584252Ethanol ethylacetateSolvent

Procedure

To a solution of 2-[4-(4-hydroxy-but-1-ynyl)-benzyl]-isoindole-1,3-dione (2.0 g, 6.55 mmol) in ethanol/ethyl acetate (3:1, 163 mL) was added palladium on carbon (10 wt. %, 1.04 g). The reaction stirred at room temperature overnight under 50 psi of hydrogen. The reaction was monitored by 1H NMR to see conversion to product. Upon completion, the reaction mixture was filtered through diatomaceous earth (Celite®), washed with ethyl acetate, and concentrated to obtain the product as a yellow oil (1.88 g, 93% yield). 1H NMR (600 MHz, CDCl3): δ 7.81 (2H, m), 7.67 (m, 2H), 7.33 (d, 2H, J=8.1 Hz), 7.10 (d, 2H, J=8.1 Hz), 4.79 (s, 2H), 3.69 (q, 3H, J=7.0 Hz), 3.60 (t, 2H, J=6.5 Hz), 2.58 (t, 2H, J=7.4 Hz), 1.64 (m, 2H), 1.55 (m, 2H); 13C NMR (150 MHz, CDCl3): 168.3, 142.2, 134.1, 134.0, 132.3, 128.8, 128.8, 123.5, 62.9, 41.5, 35.4, 32.4, 27.6.

Workup

  1. filtrationUpon completion, the reaction mixture was filtered through diatomaceous earth (Celite®)
  2. washwashed with ethyl acetate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-5adb9c2c7cbc45839341500160c8f235
Source dataset
uspto-grants-2012_09
Patent number
US08263042B2

Reaction notes

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