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

HRID 58639노트

반응식

HRID 58639 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-d234e0a59861469e8cf4dcbff74c6ff4
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09434722B2

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