Ethanol → Chloromethyl(diethoxy)phenylsilane

HRID 2413314Notes

Reaction equation

HRID 2413314 reaction equation
[Cl:1][CH2:2][Si:3](Cl)(Cl)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C(N(CC)CC)C.CC[O:21][CH2:22][CH3:23].[CH2:24]([OH:26])[CH3:25]>>[Cl:1][CH2:2][Si:3]([O:21][CH2:22][CH3:23])([O:26][CH2:24][CH3:25])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 4

HCID 702EthanolHCID 3283Diethyl EtherHCID 8471TriethylamineHCID 12747007Silane, dichloro(chloromethyl)phenyl-

Product 1

HCID 20401749Chloromethyl(diethoxy)phenylsilane

Procedure

A solution of 1.0 g (0.0044 mol) of chloromethyl(dichloro)phenylsilane in 8 ml of absolute ethanol was cooled to 0° under nitrogen and stirred while 0.61 ml (0.445 g, 0.0044 mol) of triethylamine was slowly added, giving a slurry that was allowed to warm to room temperature. Addition of 50 ml of ether, filtration to remove precipitated triethylamine/hydrochloride, and evaporation of the filtrate left a residue which was filtered through a short silica gel column (95% petroleum ether:ethyl acetate as the eluent) to give 0.80 (73%) of the title compound as a colorless oil: nmr (CDCl3): δ 1.25 (t, 6, J=6 Hz), 3.0 (s, 2), 3.9 (q, 4, J=6 Hz) and 7.2-7.9 (m, 5).

Workup

  1. additionwas slowly added
  2. customgiving a slurry that
  3. customto remove
  4. customprecipitated
  5. customtriethylamine/hydrochloride, and evaporation of the filtrate
  6. waitleft a residue which
  7. filtrationwas filtered through a short silica gel column (95% petroleum ether

Sources & evidence

ORD record
ord-6e37b5f196f941ed9b9155834a85b8bc
Source dataset
uspto-grants-1985_01
Patent number
US04496551

Reaction notes

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