4-Phenyl-1,3-dithiolane-2-thione → 2,2-diethoxy-1-(5-(2-(tetrahydro-2H-pyran-2-yloxy)propan-2-yl)-2-thioxo-1,3-dithiol-4-yl)ethanone

HRID 1778120ノート

反応式

HRID 1778120 の反応式
[CH2:1]([O:3][CH:4]([O:19][CH2:20][CH3:21])[C:5](=[O:18])[C:6]#[C:7][C:8]([CH3:17])([O:10][CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][O:12]1)[CH3:9])[CH3:2].C1(C2C[S:31][C:30](=[S:33])[S:29]2)C=CC=CC=1>ClCCl>[CH2:1]([O:3][CH:4]([O:19][CH2:20][CH3:21])[C:5]([C:6]1[S:31][C:30](=[S:29])[S:33][C:7]=1[C:8]([O:10][CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][O:12]1)([CH3:17])[CH3:9])=[O:18])[CH3:2]

参加物

4

反応物 2

HCID 2639824-Phenyl-1,3-dithiolane-2-thioneHCID 683253631,1-diethoxy-5-methyl-5-(tetrahydro-2H-pyran-2-yloxy)hex-3-yn-2-one

生成物 1

HCID 866713752,2-diethoxy-1-(5-(2-(tetrahydro-2H-pyran-2-yloxy)propan-2-yl)-2-thioxo-1,3-dithiol-4-yl)ethanone

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
130 °C

実験手順

A mixture of 1,1-diethoxy-5-methyl-5-(tetrahydro-2H-pyran-2-yloxy)hex-3-yn-2-one 3 (1.5 g, 5.0 mmol) and 4-phenyl-1,3-dithiolane-thione (5.3 g, 25.0 mmol) was heated under N2 at 130° C. for 1 hour. The reaction was monitored by thin layer chromatography using silica gel as the stationary phase and dichloromethane as the mobile phase. The color of the reaction mixture changed from yellow to dark orange. After completion of the reaction, as evidenced by TLC, the reaction was stopped, cooled, and the target compound 4 was purified by radial chromatography using silica gel as the stationary phase. The target compound 4 eluted as the third fraction with a mixture of dichloromethane and hexanes (60:40). The first band was the excess 4-phenyl-1,3-dithiolane-thione, and the second band yielded 2,2-diethoxy-1-(5-(2-(tetrahydro-2H-pyran-2-yloxy)propan-2-yl)-2-thioxo-1,3-dithiol-4-yl)ethanone 5 which was further converted to 4-(diethoxymethyl)-4-hydroxy-6,6-dimethyl-4,6-dihydro-[1,3]dithiolo[4,5-c]furan-2-thione 4.

後処理

  1. customAfter completion of the reaction
  2. temperaturecooled
  3. customthe target compound 4 was purified by radial chromatography
  4. washThe target compound 4 eluted as the third fraction with a mixture of dichloromethane and hexanes (60:40)

出典と根拠

ORDレコード
ord-6f7ce12796204c92ae8c48a25af18475
出典データセット
uspto-grants-2016_02
特許番号
US09266889B2

反応ノート

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