Hydrochloric Acid → tert-Butyldimethylsilyl chloride

HRID 256748Notes

Reaction equation

HRID 256748 reaction equation
[ClH:1].[CH3:2][Si:3]([CH3:13])([CH3:12])O[Si:5]([CH3:11])([CH3:10])[C:6]([CH3:9])([CH3:8])[CH3:7].C(N(CCCC)CCCC)CCC.S(Cl)([Cl:29])=O>>[C:6]([Si:5]([CH3:11])([CH3:10])[Cl:29])([CH3:9])([CH3:8])[CH3:7].[CH3:2][Si:3]([CH3:13])([CH3:12])[Cl:1]

Participants

6

Reactant 4

HCID 313Hydrochloric Acid2×HCID 7622TributylamineHCID 24386Thionyl Chloride3×HCID 5900171-tert-Butyl-1,1,3,3,3-pentamethyldisiloxane2×

Product 2

HCID 6397ChlorotrimethylsilaneYield 80.2%HCID 28928tert-Butyldimethylsilyl chlorideYield 86.4%

Procedure

To a 1.0 l volume reaction vessel equipped with a stirring machine, a reflux condenser, a dropping funnel and an inlet pipe for hydrogen chloride gas, there were added 204 g (1.0 mole) of pentamethyl-t-butyl-disiloxane and 9.25 g (0.050 mole) of tributylamine and 143 g (1.2 mole) of thionyl chloride was introduced into the dropping funnel. Pentamethyl-t-butyl-disiloxane was reacted with thionyl chloride at room temperature by dropwise adding thionyl chloride through the dropping funnel while supplying hydrogen chloride gas to the reaction solution. After stirring over 4 hours, the reaction solution was distilled at 125° C. to give 130 g (yield 86.4%) of t-butyldimethylchlorosilane and 87.0 g (yield 80.2%) of trimethylchlorosilane. There was not observed the formation of any viscous oily substance, the distillation temperature during the purification could substantially be decreased and the post-treatment of the reaction vessel was very easy.

Workup

  1. customTo a 1.0 l volume reaction vessel
  2. additionwas introduced into the dropping funnel
  3. distillationthe reaction solution was distilled at 125° C.

Sources & evidence

ORD record
ord-e8c96d9645f8440d8c33aa9bb5accac5
Source dataset
uspto-grants-1993_11
Patent number
US05258537

Reaction notes

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