Diethyl Ether → HCID 10397285, compound

HRID 1954463Notes

Reaction equation

HRID 1954463 reaction equation
S1C=CC=C1.C([Li])CCC.Cl[Si:12]([CH2:15][Cl:16])([CH3:14])[CH3:13].[NH4+].[Cl-].[CH2:19]([O:21][CH2:22][CH3:23])[CH3:20]>>[Cl:16][CH2:15][Si:12]([CH3:14])([CH3:13])[C:19]1[O:21][CH:22]=[CH:23][CH:20]=1

Participants

6

Reactant 5

HCID 3283Diethyl EtherHCID 8030ThiopheneHCID 25517Ammonium ChlorideHCID 74393Silane, chloro(chloromethyl)dimethyl-HCID 178418339Butyllithium

Product 1

HCID 10397285HCID 10397285, compound

Conditions

Temperature
0 °C

Procedure

Dissolve thiophene (4.76 g, 56.5 mmol) in dry diethyl ether. Add n-butyl lithium (62.2 mmol) at room temperature and stir overnight under nitrogen. Cool the mixture to 0° C., add chloro(chloromethyl)dimethylsilane (8.1 g, 56.5 mmol, in 2.5 mL diethyl ether) slowly and stir overnight under nitrogen. Add saturated NH4Cl solution to the reaction mixture. Drain off the aqueous phase and wash the organic phase with brine. Dry the organic phase over Na2SO4, filter and concentrate in vacuo. Distill the residue in a kugelrohr to afford chloromethyl(dimethyl)furylsilane (4.4 g).

Workup

  1. washwash the organic phase with brine
  2. dry with materialDry the organic phase over Na2SO4
  3. filtrationfilter
  4. concentrationconcentrate in vacuo
  5. distillationDistill the residue in a kugelrohr

Sources & evidence

ORD record
ord-5b6977208dca48828b72ed35dd268e76
Source dataset
uspto-grants-2000_09
Patent number
US06121463

Reaction notes

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