Water → HCID 13392354, compound

HRID 1980503Notes

Reaction equation

HRID 1980503 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([O:9][CH3:10])[CH:4]=1.C([Li])CCC.Cl[Si:17]([CH2:20][Cl:21])([CH3:19])[CH3:18].O>O1CCCC1.CCCCCC.C(OCC)(=O)C>[Cl:21][CH2:20][Si:17]([C:4]1[C:3]([O:2][CH3:1])=[CH:8][CH:7]=[CH:6][C:5]=1[O:9][CH3:10])([CH3:19])[CH3:18]

Participants

8

Reactant 4

HCID 962WaterHCID 90251,3-DimethoxybenzeneHCID 74393Silane, chloro(chloromethyl)dimethyl-HCID 178418339Butyllithium

Product 1

HCID 13392354HCID 13392354, compoundYield 84%

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 25.0 g (0.181 mol) of 1,3-dimethoxybenzene in 250 ml of tetrahydrofuran was stirred at room temperature under nitrogen while 125 ml (0.200 mol) of 1.6 molar n-butyllithium in hexane was added dropwise over 30 minutes. The resulting mixture was refluxed 1.5 hour, giving an orange-brown solution that was cooled to 5° and stirred while 27 ml (29.4 g, 0.205 mol) of chloro(chloromethyl)dimethylsilane was added dropwise over 15 minutes. The resulting white suspension was allowed to warm to room temperature, stirred there 1 hour, diluted with ethyl acetate, poured into water, and extracted with ether. The organic layers were washed with brine, dried over magnesium sulfate, and distilled to give 37.0 g (84%) of the title compound as a colorless liquid: bp 98°-110° (0.1 mm); nmr (CDCl3) 0.4 (6H, s), 3.1 (2H, s), 3.7 (6H, s), 6.3 (2 H, d), 7.1 (1H, m).

Workup

  1. additionwas added dropwise over 30 minutes
  2. temperatureThe resulting mixture was refluxed 1.5 hour
  3. customgiving an orange-brown solution that
  4. temperaturewas cooled to 5°
  5. additionwas added dropwise over 15 minutes
  6. extractionextracted with ether
  7. washThe organic layers were washed with brine
  8. dry with materialdried over magnesium sulfate
  9. distillationdistilled

Sources & evidence

ORD record
ord-214ad6aee2744122ae8519ebd20752bb
Source dataset
uspto-grants-1985_04
Patent number
US04510136

Reaction notes

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