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

HRID 581617ノート

反応式

HRID 581617 の反応式
[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]

参加物

5

反応物 1

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 7047Quinoline触媒HCID 131709914Lindlars catalyst触媒HCID 702Ethanol溶媒

実験手順

13.04 g (63.7 mmol) of (R)-1-Chloro-6-trimethylsilanyl-hex-4-yn-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)-1-chloro-6-trimethylsilanyl-hex-4-en-2-ol as colorless oil.

後処理

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

出典と根拠

ORDレコード
ord-42bf17d26e4b4d0f896ad9be2906c112
出典データセット
uspto-grants-1999_07
特許番号
US05919986

反応ノート

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