Potassium tert-butoxide → HCID 68944701, compound

HRID 242715Notes

Reaction equation

HRID 242715 reaction equation
[Br-].[CH3:2][C:3]1[C:28]([CH3:29])=[CH:27][CH:26]=[CH:25][C:4]=1[CH2:5][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CC(C)([O-])C.[K+].[O:36]=[C:37]1[C:45]2[C:40](=[CH:41][CH:42]=[CH:43][CH:44]=2)[C:39](=[O:46])[N:38]1[CH2:47][CH2:48][CH2:49][C:50]1[CH:51]=[C:52]([CH:55]=[CH:56][CH:57]=1)[CH:53]=O>C(Cl)Cl.C1COCC1>[CH3:2][C:3]1[C:28]([CH3:29])=[CH:27][CH:26]=[CH:25][C:4]=1/[CH:5]=[CH:53]\[C:52]1[CH:51]=[C:50]([CH2:49][CH2:48][CH2:47][N:38]2[C:39](=[O:46])[C:40]3[C:45](=[CH:44][CH:43]=[CH:42][CH:41]=3)[C:37]2=[O:36])[CH:57]=[CH:56][CH:55]=1

Participants

6

Reactant 3

HCID 23665647Potassium tert-butoxideHCID 577664653-(3-(1,3-Dioxoisoindolin-2-yl)propyl)benzaldehydeHCID 86632150HCID 86632150, compound

Product 1

HCID 68944701HCID 68944701, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To an ice cold solution of 2,3-dimethylbenzyltriphenylphosphonium bromide (1.1197 g, 2.43 mmol) in CH2Cl2 (10 mL) was added a solution of potassium tert-butoxide (2.5 mL of a 1 M solution in THF, 2.5 mmol). The mixture was stirred for 5 min, then a solution of phthalimide 29 (0.3380 g, 1.15 mmol) in CH2Cl2 (10 mL) was added. The mixture was warmed to room temperature, stirred for 20 min then concentrated under reduced pressure. 10% EtOAc-heptane was added and the solids were removed by filtration. The filtrate was concentrated under reduced pressure. Purification by repeated flash chromatography (6 to 40% EtOAc-hexanes gradient then 10% EtOAc-hexanes) gave (Z)-2-(3-(3-(2,3-dimethylstyryl)phenyl)propyl)isoindoline-1,3-dione as an oil. Yield (0.1871 g, 41%), trans-/cis-isomer ratio 1:11.7. Cis-isomer: 1H NMR (400 MHz, CDCl3) δ 7.85 (dd, J=5.6, 2.8 Hz, 2H), 7.72 (dd, J=5.2, 3.2 Hz, 2H), 7.04 (t, J=7.6 Hz, 1H), 6.88-6.98 (m, 6H), 6.68 (d, J=12.0 Hz, 1H), 6.56 (d, J=12.0 Hz, 1H), 3.64 (t, J=7.2 Hz, 2H), 2.52 (t, J=7.6 Hz, 2H), 2.52 (s, 3H), 2.17 (s, 3H), 1.80-1.88 (m, 2H).

Workup

  1. stirringstirred for 20 min
  2. concentrationthen concentrated under reduced pressure
  3. addition10% EtOAc-heptane was added
  4. customthe solids were removed by filtration
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customPurification by repeated flash chromatography (6 to 40% EtOAc-hexanes

Sources & evidence

ORD record
ord-3acf9943545f480e910fcf677fc9df1b
Source dataset
uspto-grants-2014_02
Patent number
US08653142B2

Reaction notes

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