4-Toluenesulfonyl chloride → 2-Cyano-1-(2-furyl)vinyl 4-methylbenzenesulfonate

HRID 1926016노트

반응식

HRID 1926016 반응식
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6](=[O:10])[CH2:7][C:8]#[N:9].[C:11]1([CH3:21])[CH:16]=[CH:15][C:14]([S:17](Cl)(=[O:19])=[O:18])=[CH:13][CH:12]=1.C(N(CC)CC)C>ClCCl>[CH3:21][C:11]1[CH:16]=[CH:15][C:14]([S:17]([O:10][C:6]([C:2]2[O:1][CH:5]=[CH:4][CH:3]=2)=[CH:7][C:8]#[N:9])(=[O:19])=[O:18])=[CH:13][CH:12]=1

참가 물질

5

반응물 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 1416712-Furoylacetonitrile

생성물 1

HCID 545345202-Cyano-1-(2-furyl)vinyl 4-methylbenzenesulfonate수율 92.5%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

To a mixture of 3-(2-furyl)-3-oxopropanenitrile (5.29 g), p-toluenesulfonyl chloride (9.00 g) and dichloromethane (60 mL) was added dropwise triethylamine (5.99 g) under ice-cooling. After stirring under ice-cooling for 1.5 hrs, the mixture was diluted with dichloromethane (100 mL). The mixture was washed with water (150 mL), dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent, hexane:methyl acetate=9:1→3:1) to give the title compound (10.48 g) as a mixture of (E)-form and (Z)-form (3:1).

후처리

  1. temperaturecooling
  2. temperaturecooling for 1.5 hrs
  3. washThe mixture was washed with water (150 mL)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (eluent, hexane:methyl acetate=9:1→3:1)

출처 및 근거

ORD 기록
ord-bce5a5ff40db43af83147ea981bbda45
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08178543B2

반응 노트

불러오는 중…