Methanol → 1,4-Dichloro-2-(trimethoxy)silyl-2-butene

HRID 1904348Notes

Reaction equation

HRID 1904348 reaction equation
[Cl:1][CH2:2][C:3]([Si:7](Cl)(Cl)Cl)=[CH:4][CH2:5][Cl:6].C1[CH2:15][O:14]CC1.[CH3:16][OH:17].N(CC)(CC)CC.CC[O:27][CH2:28]C>>[Cl:1][CH2:2][C:3]([Si:7]([O:14][CH3:15])([O:27][CH3:28])[O:17][CH3:16])=[CH:4][CH2:5][Cl:6]

Participants

6

Reactant 5

HCID 887MethanolHCID 3283Diethyl EtherHCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 53421800Trichloro(1,4-dichlorobut-2-en-2-yl)silane

Product 1

HCID 544102631,4-Dichloro-2-(trimethoxy)silyl-2-buteneYield 80%

Procedure

A solution of 14.2 g (55 mmol) of 1,4-dichloro-2-(trichloro)silyl-2-butene [VI]in 7 ml of THF was cooled to -10° C., to which was slowly added dropwise a mixed solution of 10 ml of CH3OH (55×3×1.5 mmol) and 34.5 ml of (C2H5)3N (55 x 3 x 1.5 mmol). Then, it was stirred at room temperature for one hour and 30 ml of dry ether were added. After filtering out the (C2H5)3N·HCl and removing the solvent through distillation under a reduced pressure, 10.8 g of 1,4-dichloro-2-(trimethoxy)silyl-2-butene [VII](yield: 80 %, bp: 88°-90° C./1-2 mmHg).

Workup

  1. filtrationAfter filtering out the (C2H5)3N·HCl
  2. customremoving the solvent

Sources & evidence

ORD record
ord-fd685ebaf13d47f39f6444a89b19df03
Source dataset
uspto-grants-1989_06
Patent number
US04837339

Reaction notes

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