Potassium tert-butoxide → HCID 68940474, compound

HRID 1967698Notes

Reaction equation

HRID 1967698 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][CH2:14][C:15]1[CH:16]=[C:17]([CH:20]=[CH:21][CH:22]=1)[CH:18]=O.[Br-].[CH2:24]([O:26][C:27]1[CH:52]=[CH:51][CH:50]=[C:49]([O:53][CH2:54][CH3:55])[C:28]=1[CH2:29][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[CH3:25].CC(C)([O-])C.[K+]>C1COCC1>[CH2:54]([O:53][C:49]1[CH:50]=[CH:51][CH:52]=[C:27]([O:26][CH2:24][CH3:25])[C:28]=1/[CH:29]=[CH:18]/[C:17]1[CH:16]=[C:15]([CH2:14][CH2:13][CH2:12][N:3]2[C:4](=[O:11])[C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[C:2]2=[O:1])[CH:22]=[CH:21][CH:20]=1)[CH3:55]

Participants

5

Reactant 3

HCID 23665647Potassium tert-butoxideHCID 577664653-(3-(1,3-Dioxoisoindolin-2-yl)propyl)benzaldehydeHCID 86632160HCID 86632160, compound

Product 1

HCID 68940474HCID 68940474, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To an ice-cold mixture of phthalimide 29 (0.440 g, 1.5 mmol) in THF (25 mL) was added (2,6-diethoxybenzyl)triphenylphosphonium bromide (0.860 g, 1.65 mmol) and potassium tert-butoxide (0.336 g, 3.0 mmol) portionwise. The reaction was allowed to warm to room temperature and stirred for 2 h. The mixture was then quenched with water and extracted with EtOAc. The combined organics were washed with brine, dried over Na2SO4 and concentrated under reduced pressure. Purification by flash chromatography (7% EtOAc-hexanes) gave (E)-2-(3-(3-(2,6-diethoxystyryl)phenyl)propyl)isoindoline-1,3-dione as a brown oil. Yield (0.055 g, 8%): 1H NMR (400 MHz, CDCl3) δ 7.80-7.83 (m, 2H), 7.67-7.70 (m, 2H), 7.62 (d, J=16.8 Hz, 1H), 7.45 (d, J=16.8 Hz, 1H), 7.29-7.31 (m, 1H), 7.22 (t, J=7.6 Hz, 1H), 7.17 (d, J=6.4 Hz, 1H), 7.11 (t, J=8.4 Hz, 1H), 7.06 (d, J=7.2 Hz, 1H), 6.60 (d, J=8.4 Hz, 2H), 4.11 (dt, J=7.2, 6.8 Hz, 4H), 3.78 (t, J=7.2 Hz, 2H), 2.71 (t, J=7.6 Hz, 2H), 2.03-2.11 (m, 2H), 1.50 (t, J=7.2 Hz, 6H).

Workup

  1. customThe mixture was then quenched with water
  2. extractionextracted with EtOAc
  3. washThe combined organics were washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customPurification by flash chromatography (7% EtOAc-hexanes)

Sources & evidence

ORD record
ord-7beca3ac00414c56b110e5ceac16bb2e
Source dataset
uspto-grants-2013_04
Patent number
US08420863B2

Reaction notes

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