Tetrahydrofuran → 3,3,5-Trimethyl-3,5-disila-1-hexene

HRID 1608888Notes

Reaction equation

HRID 1608888 reaction equation
ClC[Si:3]([CH3:6])([CH3:5])[CH3:4].Cl[SiH2:8][CH:9]=C(C)C.[C:13](OC)([CH3:16])(C)C.[CH2:19]1COCC1>>[CH3:19][Si:8]([CH3:9])([CH2:4][SiH:3]([CH3:6])[CH3:5])[CH:13]=[CH2:16]

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 15413tert-Butyl methyl etherHCID 75361Silane, (chloromethyl)trimethyl-HCID 57370515C4H9ClSi

Product 1

HCID 1231834723,3,5-Trimethyl-3,5-disila-1-hexeneYield 72%

Procedure

In a procedure analogous to the above paragraph, a Grignard solution was prepared from 68 g (0.55 mol) of chloromethyltrimethylsilane in 150 ml of THF and was then added dropwise at 10° C. to a solution containing chlorodimethylvinylsilane, (available from ABCR GmbH, 7500 Karlsruhe) (2 hours). The mixture was then warmed to room temperature and finally kept at 35° C. for 1 hour, during which a voluminous precipitate formed. Hydrolysis, extraction by shaking with methyl tertbutyl ether, phase separation and working up resulted in 106 g of crude product which on fractionation yielded 68 g (corresponding to 72% of theory) of 3,3,5-trimethyl-3,5-disila-1-hexene (C8H20Si2) at 149°-151° C.

Workup

  1. additionwas then added dropwise at 10° C. to a solution
  2. customa voluminous precipitate formed
  3. customHydrolysis, extraction
  4. customworking up resulted in 106 g of crude product which on fractionation

Sources & evidence

ORD record
ord-14a53360492d40dcbdd1eb40048a562d
Source dataset
uspto-grants-1995_03
Patent number
US05399290

Reaction notes

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