Diethyl Ether → HCID 13392467, compound

HRID 2413312Notes

Reaction equation

HRID 2413312 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([SiH:8]([C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=2)[O:9]C(C)C)=[CH:4][CH:3]=1.[Na].[NH:21]1[CH:25]=[CH:24][N:23]=[CH:22]1.[CH3:26]COCC>CN(C)C=O.C(OCC)(=O)C>[Cl:19][C:16]1[CH:15]=[CH:14][C:13]([Si:8]([C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=2)([OH:9])[CH2:26][N:21]2[CH:25]=[CH:24][N:23]=[CH:22]2)=[CH:18][CH:17]=1

Participants

6

Reactant 3

HCID 3283Diethyl EtherHCID 57373095Imidazole sodiumHCID 131714092HCID 131714092, compound

Product 1

HCID 13392467HCID 13392467, compoundYield 19%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 5.5 g (15.3 mmol) of chloromethyl[bis(4-chlorophenyl](2-propoxy)silane and 1.5 g (17 mmol) of imidazole sodium salt in dimethylformamide was warmed to 80° to 90° for 2 hours, cooled, diluted with ethyl acetate, washed three times with water and once with brine, dried over magnesium sulfate, and evaporated to leave a viscous oil. Trituration with ether gave 1.0 g (19%) of the title compound as a colorless solid: m.p. 131°-133°; nmr (CD3SOCD3) 4.1 (2H, s), 6.8 (1H, s), 6.9 (1H, s), 7.4 (4H, d), 7.6 (5H, d).

Workup

  1. temperaturewas warmed to 80° to 90° for 2 hours
  2. temperaturecooled
  3. washwashed three times with water
  4. dry with materialonce with brine, dried over magnesium sulfate
  5. customevaporated
  6. customto leave a viscous oil

Sources & evidence

ORD record
ord-06067153813640dfb6080e2012551385
Source dataset
uspto-grants-1985_01
Patent number
US04496551

Reaction notes

Loading…