Tetrahydrofuran → Chloropropyldimethylvinylsilane

HRID 1170068

Reaction equation

HRID 1170068 reaction equation
C([Mg]Br)=C.[Cl:5][CH2:6][CH2:7][CH2:8][Si:9]([CH3:12])(C)Cl.[CH2:13]1[CH2:17]OC[CH2:14]1>>[Cl:5][CH2:6][CH2:7][CH2:8][SiH2:9][CH:12]=[C:13]([CH3:17])[CH3:14]

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 82765Silane, chloro(3-chloropropyl)dimethyl-HCID 178418507HCID 178418507, compound

Product 1

HCID 131715857ChloropropyldimethylvinylsilaneYield 66.49%

Procedure

To a stirred solution of 1 M vinyl magnesium bromide in THF (9.1 L), 3-chloropropyl dimethylchlorosilane (1.5 Kg) was added over the period of 3 hr through an addition. The reaction mixture stirred further for 2 hr. Added D.M water (9.1 L) and separated the organic layer. The hazy aqueous layer was filtered through hyflo bed and extracted with dichloromethane (3.0 L). The dichloromethane extract was mixed with organic layer and evaporated to dryness to give yellow liquid which was distilled using a Vigreaux column to get pure colorless title product (0.986 Kg)

Workup

  1. customAdded D.M water (9.1 L) and separated the organic layer
  2. filtrationThe hazy aqueous layer was filtered through hyflo bed
  3. extractionextracted with dichloromethane (3.0 L)
  4. extractionThe dichloromethane extract
  5. additionwas mixed with organic layer
  6. customevaporated to dryness
  7. customto give yellow liquid which
  8. distillationwas distilled

Sources & evidence

ORD record
ord-b4d53911fb1348868ab25b31f34d2f40
Source dataset
uspto-grants-2010_11
Patent number
US07825257B1

Linked notes

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