Tetrahydrofuran → (Z)-(R)-trimethyl-(4-oxiranyl-but-2-enyl)silane

HRID 581618Notes

Reaction equation

HRID 581618 reaction equation
Cl[CH2:2][C@H:3]([OH:12])[CH2:4]/[CH:5]=[CH:6]\[CH2:7][Si:8]([CH3:11])([CH3:10])[CH3:9].C1COCC1.[OH-].[K+]>O>[CH3:9][Si:8]([CH3:11])([CH3:10])[CH2:7]/[CH:6]=[CH:5]\[CH2:4][C@@H:3]1[CH2:2][O:12]1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14797Potassium HydroxideHCID 86754181(Z)-(R)-1-chloro-6-trimethylsilanyl-hex-4-en-2-ol

Product 1

HCID 86754182(Z)-(R)-trimethyl-(4-oxiranyl-but-2-enyl)silaneYield 98.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

12.97 g (62.7 mmol) of (Z)-(R)-1-Chloro-6-trimethylsilanyl-hex-4-en-2-ol was dissolved in 215 ml of abs. THF. A solution of 60.34 g (1.08 mol) of KOH in 61 g of water was added ant the heterogeneous mixture stirred at 30° for 24h, until GC analysis indicated the disappearance of the starting chlorohydrine. The reaction mixture was then poured onto crushed ice/NH4Cl, extracted with ether, dried over sodium sulfate, and the solvents removed i.V. Thereby, 10.5 g of (Z)-(R)-trimethyl-(4-oxiranyl-but-2-enyl)-silane was isolated, 93% pure according to GC, which was used as such for the next step.

Workup

  1. additionThe reaction mixture was then poured
  2. extractionextracted with ether
  3. dry with materialdried over sodium sulfate
  4. customthe solvents removed i.V

Sources & evidence

ORD record
ord-dca77387363c40a29e7be47e55278e8d
Source dataset
uspto-grants-1999_07
Patent number
US05919986

Reaction notes

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