Sodium ethoxide → 3-[Ethoxy(dimethyl)silyl]propane-1-thiol

HRID 1466967Notes

Reaction equation

HRID 1466967 reaction equation
C([S:4][CH2:5][CH2:6][CH2:7][Si:8]([O:11][CH2:12][CH3:13])([CH3:10])[CH3:9])(=O)C.CC[O-].[Na+]>C(O)C>[SH:4][CH2:5][CH2:6][CH2:7][Si:8]([O:11][CH2:12][CH3:13])([CH3:10])[CH3:9]

Participants

4

Reactant 2

HCID 2723922Sodium ethoxideHCID 59365620HCID 59365620, compound

Product 1

HCID 222272273-[Ethoxy(dimethyl)silyl]propane-1-thiolYield 66%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Added, at ambient temperature, to a solution of S-(ethanoyl)mercaptopropylethoxydimethylsilane C (65.4 g, 0.297 mol) in absolute ethanol (230 ml) is solid sodium ethylate (2.02 g, 0.030 mol) under argon. The reaction medium is brought to reflux for 2.5 hours. After returning to ambient temperature, the precipitate of NaCl is filtered and washed with heptane (350 ml). After evaporating the solvents under reduced pressure at 45° C., the oil obtained is purified by vacuum distillation (60° C./10 mbar). The 3-mercaptopropylethoxydimethylsilane D with CAS number [141137-15-7] (34.7 g, 0.195 mol) is obtained with a yield of 66%.

Workup

  1. temperatureto reflux for 2.5 hours
  2. customAfter returning to ambient temperature
  3. filtrationthe precipitate of NaCl is filtered
  4. washwashed with heptane (350 ml)
  5. customAfter evaporating the solvents under reduced pressure at 45° C.
  6. customthe oil obtained
  7. distillationis purified by vacuum distillation (60° C./10 mbar)

Sources & evidence

ORD record
ord-f3d24dadaf68443183f854cf8327cb92
Source dataset
uspto-grants-2015_04
Patent number
US09000092B2

Reaction notes

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