Chlorosuccinimide → Tert-butyl(2-(5-chlorothiophen-2-yl)ethoxy)dimethylsilane

HRID 446383Notes

Reaction equation

HRID 446383 reaction equation
C1C(=O)N([Cl:8])C(=O)C1.[C:9]([Si:13]([CH3:23])([CH3:22])[O:14][CH2:15][CH2:16][C:17]1[S:18][CH:19]=[CH:20][CH:21]=1)([CH3:12])([CH3:11])[CH3:10]>C(Cl)(Cl)Cl.C(Cl)Cl>[C:9]([Si:13]([O:14][CH2:15][CH2:16][C:17]1[S:18][C:19]([Cl:8])=[CH:20][CH:21]=1)([CH3:23])[CH3:22])([CH3:10])([CH3:12])[CH3:11]

Participants

5

Reactant 2

HCID 31398ChlorosuccinimideHCID 22503634Tert-butyldimethyl(2-(thiophen-2-YL)ethoxy)silane

Product 1

HCID 57989349Tert-butyl(2-(5-chlorothiophen-2-yl)ethoxy)dimethylsilane

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

NCS (0.826 g) was added portionwise to a solution of tert-butyldimethyl(2-(thiophen-2-yl)ethoxy)silane [WO 2008096129] (1.5 g) in chloroform (50 mL) and the resulting mixture was heated at reflux for 3 days. The mixture was diluted with DCM (100 mL) and washed with saturated aqueous sodium bicarbonate (2×100 mL) and brine (100 mL), then dried over sodium sulphate, filtered and evaporated. The residue was purified by silica gel chromatography eluting with isohexane to give the subtitled compound as a clear oil. Yield 1.00 g.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureat reflux for 3 days
  3. washwashed with saturated aqueous sodium bicarbonate (2×100 mL) and brine (100 mL)
  4. dry with materialdried over sodium sulphate
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by silica gel chromatography
  8. washeluting with isohexane

Sources & evidence

ORD record
ord-43ca3383236e41dc81573665ebdc55f8
Source dataset
uspto-grants-2013_07
Patent number
US08476265B2

Reaction notes

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