Potassium Carbonate → HCID 20195684, compound

HRID 653168Notes

Reaction equation

HRID 653168 reaction equation
[CH:1]1[C:4]2[CH:5]=[CH:6][C:7]([N:9]3[C:13](=[O:14])[C:12]4=[CH:15][C:16]([C:19]#[C:20][Si](C)(C)C)=[CH:17][CH:18]=[C:11]4[C:10]3=[O:25])=[CH:8][C:3]=2[CH:2]=1.C(=O)([O-])[O-].[K+].[K+]>>[CH:1]1[C:4]2[CH:5]=[CH:6][C:7]([N:9]3[C:13](=[O:14])[C:12]4=[CH:15][C:16]([C:19]#[CH:20])=[CH:17][CH:18]=[C:11]4[C:10]3=[O:25])=[CH:8][C:3]=2[CH:2]=1

Participants

3

Reactant 2

HCID 11430Potassium CarbonateHCID 20195687HCID 20195687, compound

Product 1

HCID 20195684HCID 20195684, compound

Procedure

A mixture of N-4-benzocyclobutenyl 4-trimethylsilylethynyl phthalimide (3.95 g, 11.4 mmol) and potassium carbonate (0.50 g, 3.62 mmol) was stirred in 100 ml of anhydrous methol under N2 at room temperature for about 3 hours. The solvent was then removed, and the residue was treated with 75 ml of H2O and 50 ml CH2Cl2. The methylene chloride layer was separated and the aqueous layer was extracted with CH2Cl2 (2×50 ml). The combined extract was dried over MgSO4, and then filtered through a bed of silica gel (10 g). Slow evaporation of the filtrate led to the isolation of light yellow crystals. Yield: 2.85 g (91%) m.p.=191°-192° . Calc. for C18H11NO2 : 79.10% C; 4.06% H; 5.12% N, Found: 78.98% C; 4.01% H; 5.09% N. Mass Spectroscopy: 273 (M+ 100 %). Proton NMR (CDCl3): 3.25 (singlet, alicyclic protons); 3.37 (singlet,≡CH); 7.08-7.31, 7.94-8.08 (complex, aromatic protons). IR(KBr): 3272s (≡CH stretch); 2943m (alicyclic CH stretch); 1710 ms, 1773 vs (symmetric and asymmetric stretches of imide group).

Workup

  1. customThe solvent was then removed
  2. additionthe residue was treated with 75 ml of H2O and 50 ml CH2Cl2
  3. customThe methylene chloride layer was separated
  4. extractionthe aqueous layer was extracted with CH2Cl2 (2×50 ml)
  5. extractionThe combined extract
  6. dry with materialwas dried over MgSO4
  7. filtrationfiltered through a bed of silica gel (10 g)
  8. customevaporation of the filtrate
  9. custom1710 ms, 1773 vs (symmetric and asymmetric stretches of imide group)

Sources & evidence

ORD record
ord-2612f6a6369b4bd994fab097592d9339
Source dataset
uspto-grants-1987_06
Patent number
US04675370

Reaction notes

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