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

HRID 1604842Notes

Reaction equation

HRID 1604842 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-4en-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 24 h, 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-74316c5a3c3b4f9a9703584e4039bf68
Source dataset
uspto-grants-1999_11
Patent number
US05994569

Reaction notes

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