Imidazole → HCID 21709889, compound

HRID 650881Notes

Reaction equation

HRID 650881 reaction equation
[CH:1]1([Si:7]([CH3:10])([CH3:9])Cl)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.N1C=CN=C1.[CH2:16]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH2:18][C:17]1=[O:25].O>CN(C=O)C>[CH:1]1([Si:7]([CH3:10])([CH3:9])[O:25][C:17]2[CH2:18][C:19]3[C:24]([CH:16]=2)=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 119832-IndanoneHCID 564559Chlorocyclohexyldimethylsilane

Product 1

HCID 21709889HCID 21709889, compoundYield 68.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of cyclohexyldimethylchlorosilane (84.62 g, 478.7 mmol) and imidazole (32.59 g, 478.7 mmol) in DMF (300 mL) was reacted with 2-indanone (57.62 g, 436.0 mmol). The reaction mixture was stirred overnight at room temperature, treated with water (300 mL) and extracted with Et2O (3×200 mL). The combined organic phases were washed with water (3×300 mL) and dried over sodium sulfate. The solvents were removed to leave an orange oil. Distillation under reduced pressure gave 81.67 g (68.8%) of the title compound as a yellow oil (bp. 140-142° C./0.2 mbar). 1H NMR (CDCl3, δ): 7.25-7.11 (m, 3H); 7.01 (td, 3J=7.3 Hz, 4J=1.4 Hz, 1H); 5.76 (d, 4J=0.7 Hz, 1H); 3.29 (s, 2H) 1.77-1.74 (m, 5H); 1.27-1.13 (m, 5H); 0.90 (m, 1H); 0.24 (s, 6H). 13C NMR (CDCl3, δ): 162.44; 145.24; 136.60; 126.47; 123.07; 122.37; 118.91; 106.32; 39.52; 27.69; 26.77; 26.46; 26.33; −3.55.

Workup

  1. extractionextracted with Et2O (3×200 mL)
  2. washThe combined organic phases were washed with water (3×300 mL)
  3. dry with materialdried over sodium sulfate
  4. customThe solvents were removed
  5. customto leave an orange oil
  6. distillationDistillation under reduced pressure

Sources & evidence

ORD record
ord-fb60699c66874b629ae0a7989c2c9f0f
Source dataset
uspto-grants-2001_08
Patent number
US06277778B1

Reaction notes

Loading…