Ethyl Acetate → (1,1'-Biphenyl-4-yl)dimethyl(1H-imidazol-1-ylmethyl)silane

HRID 2413306Notes

Reaction equation

HRID 2413306 reaction equation
[C:1]1([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][C:4]([Si:7]([CH2:10]Cl)([CH3:9])[CH3:8])=[CH:3][CH:2]=1.[Na].[NH:19]1[CH:23]=[CH:22][N:21]=[CH:20]1.C(OCC)(=O)C>CN(C)C=O.O>[C:1]1([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][C:4]([Si:7]([CH3:9])([CH3:8])[CH2:10][N:19]2[CH:23]=[CH:22][N:21]=[CH:20]2)=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 13392351HCID 13392351, compoundHCID 57373095Imidazole sodium

Product 1

HCID 13392415(1,1'-Biphenyl-4-yl)dimethyl(1H-imidazol-1-ylmethyl)silaneYield 29%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 2.6 g (0.010 mol) of (1,1'-biphenyl-4-yl)chloromethyldimethylsilane and 1.1 g (0.012 mol) of imidazole sodium salt in 5 ml of dimethylformamide was warmed to 80°-90° for 2 hours, cooled, diluted with water, and extracted with ether. The ether solution was washed with water and brine, dried over magnesium sulfate, and evaporated to leave 2.0 g of a viscous, pale yellow oil. Trituration of a small sample with hexanes gave a solid. The bulk of the crude product was then taken up in a hot mixture of 20 ml of hexanes and 3 ml of ethyl acetate, the solution was cooled slowly, and seed crystals were added when cloudiness was observed. The resulting crystals were collected and dried to give 0.84 g (29%) of the title compound as colorless flakes: m.p. 51°-53°; ir (NujolR) 1235, 1215, 1105, 1065, 900, 830, 785, 750, 730, 685 cm-1 ; nmr (CDCl3) 0.4 (6 H, s), 3.7 (2H, s), 6.7 (1H, broad s), 7.0 (1H, broad s), 7.1-7.8 (10H, m); analysis for C18H20N2Si (mw 292.45):

Workup

  1. temperaturewas warmed to 80°-90° for 2 hours
  2. temperaturecooled
  3. extractionextracted with ether
  4. washThe ether solution was washed with water and brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated
  7. customto leave 2.0 g of a viscous, pale yellow oil
  8. temperaturethe solution was cooled slowly
  9. additionseed crystals were added when cloudiness
  10. customThe resulting crystals were collected
  11. customdried

Sources & evidence

ORD record
ord-b9af86aa563546c181da10bad53a0220
Source dataset
uspto-grants-1985_01
Patent number
US04496551

Reaction notes

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