(R)-1-Chloro-6-trimethylsilanyl-hex-4-yn-2-ol → (Z)-(R)-1-chloro-6-trimethylsilanyl-hex-4-en-2-ol

HRID 1604841Notes

Reaction equation

HRID 1604841 reaction equation
[Cl:1][CH2:2][C@H:3]([OH:12])[CH2:4][C:5]#[C:6][CH2:7][Si:8]([CH3:11])([CH3:10])[CH3:9]>N1C2C(=CC=CC=2)C=CC=1.[Pd].CC([O-])=O.CC([O-])=O.[Pb+2].CCO>[Cl:1][CH2:2][C@H:3]([OH:12])[CH2:4]/[CH:5]=[CH:6]\[CH2:7][Si:8]([CH3:9])([CH3:10])[CH3:11]

Participants

5

Reactant 1

HCID 21310064(R)-1-Chloro-6-trimethylsilanyl-hex-4-yn-2-ol

Product 1

HCID 86754181(Z)-(R)-1-chloro-6-trimethylsilanyl-hex-4-en-2-olYield 98.5%

Reagents, catalysts & solvents 3

HCID 7047QuinolineCatalystHCID 131709914Lindlars catalystCatalystHCID 702EthanolSolvent

Procedure

13.04 g (63.7 mmol) of (R)-1-Chloro-6-trimethylsilanyl-hex-4yn-2-ol was dissolved in 260 ml of abs. EtOH and hydrogenated, in the presence of 9 drops of quinoline, over 1.70 g of Lindlar catalyst at ambient temperature and 1 atm of H2. The progress of the reaction was followed by GC. After 2 h the reaction mixture was filtered and the solvent removed i.V. Short flash chromatography (SiO2, hexane/AcOEt=85/15) afforded 12.97 g of (Z)-(R)-l-chloro-6-trimethylsilanyl-hex-4-en-2-ol as colorless oil.

Workup

  1. customat ambient temperature
  2. filtrationAfter 2 h the reaction mixture was filtered
  3. customthe solvent removed i.V

Sources & evidence

ORD record
ord-9d3adaae61fd4c73b7fbf3bae00cd45c
Source dataset
uspto-grants-1999_11
Patent number
US05994569

Reaction notes

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