Imidazole → HCID 21709886, compound

HRID 650880Notes

Reaction equation

HRID 650880 reaction equation
[C:1]([Si:7]([CH3:10])([CH3:9])Cl)([CH:4](C)[CH3:5])([CH3:3])[CH3:2].N1C=CN=[CH:12]1.[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>[C:1]([Si:7]([CH3:10])([CH3:9])[O:25][C:17]1[CH2:18][C:19]2[C:24]([CH:16]=1)=[CH:23][CH:22]=[CH:21][CH:20]=2)([CH2:4][CH2:5][CH3:12])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 119832-IndanoneHCID 144239Dimethylthexylsilyl chloride

Product 1

HCID 21709886HCID 21709886, compoundYield 83.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of thexyldimethylchlorosilane (100.0 g, 559.3 mmol) and imidazole (38.08 g, 559.3 mmol) in DMF (350 mL) was reacted with 2-indanone (67.40 g, 510.0 mmol) and then stirred for two days at room temperature. The reaction mixture was treated with water (300 mL). and extracted with Et2O (3×200 mL). The combined organic phases were washed with water (2×200 mL) and dried over sodium sulfate. Evaporation of the solvents left a red oil. Distillation under reduced pressure gave 116.89 g (83.5%) of the title compound as a yellow oil (bp. 128-130° C./0.4 mbar). 1H NMR (CDCl3, δ): 7.24-7.10 (m, 3H); 7.00 (td, 3J=7.3 Hz, 4J=1.3 Hz, 1H); 5.74 (d, 4J=0.6 Hz, 1H); 3.28 (s, 2H); 1.70 (sept, 3J=6.8 Hz, 1H); 0.93 (s, 6H); 0.92 (d, 3J=6.8 Hz, 6H); 0.29 (s, 6H). 13C NMR (CDCl3, δ): 162.82; 145.71; 137.03; 126.86; 123.45; 122.73; 119.29; 106.92; 40.00; 34.49; 25.51; 20.51; 18.89; −2.26.

Workup

  1. extractionand extracted with Et2O (3×200 mL)
  2. washThe combined organic phases were washed with water (2×200 mL)
  3. dry with materialdried over sodium sulfate
  4. customEvaporation of the solvents
  5. waitleft a red oil
  6. distillationDistillation under reduced pressure

Sources & evidence

ORD record
ord-e4cb6d08942f401ea38638f6821dab69
Source dataset
uspto-grants-2001_08
Patent number
US06277778B1

Reaction notes

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