Pyridine → 4-(Triethylsilyl)but-3-yn-1-yl 4-methylbenzene-1-sulfonate

HRID 58639ノート

反応式

HRID 58639 の反応式
[CH2:1]([Si:3]([CH2:11][CH3:12])([CH2:9][CH3:10])[C:4]#[C:5][CH2:6][CH2:7][OH:8])[CH3:2].[C:13]1([CH3:23])[CH:18]=[CH:17][C:16]([S:19](Cl)(=[O:21])=[O:20])=[CH:15][CH:14]=1.N1C=CC=CC=1>ClCCl>[CH3:23][C:13]1[CH:18]=[CH:17][C:16]([S:19]([O:8][CH2:7][CH2:6][C:5]#[C:4][Si:3]([CH2:1][CH3:2])([CH2:9][CH3:10])[CH2:11][CH3:12])(=[O:21])=[O:20])=[CH:15][CH:14]=1

参加物

5

反応物 3

HCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 27606944-(Triethylsilyl)-3-butyn-1-ol

生成物 1

HCID 120301384-(Triethylsilyl)but-3-yn-1-yl 4-methylbenzene-1-sulfonate収率 102.5%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A solution of 4-(triethylsilyl)but-3-yn-1-ol (2 mL; 9.22 mmol), p-toluensulfonyl chloride (3.52 g; 18.44 mmol) and pyridine (1.49 mL; 18.44 mmol) in dichloromethane (30 mL) was stirred at room temperature for 3 days. The reaction mixture was then washed with a saturated solution of sodium hydrogen sulphate and brine. The organic layer was dried, concentrated under reduced pressure and the crude material was purified by flash chromatography on silica gel (eluent 2 to 20% ethyl acetate in heptane) to yield 3.20 g (quantitative yield) of 4-(triethylsilyl)but-3-ynyl 4-methylbenzenesulfonate as a yellow oil.

後処理

  1. washThe reaction mixture was then washed with a saturated solution of sodium hydrogen sulphate and brine
  2. customThe organic layer was dried
  3. concentrationconcentrated under reduced pressure
  4. customthe crude material was purified by flash chromatography on silica gel (eluent 2 to 20% ethyl acetate in heptane)

出典と根拠

ORDレコード
ord-d234e0a59861469e8cf4dcbff74c6ff4
出典データセット
uspto-grants-2016_09
特許番号
US09434722B2

反応ノート

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