Methanesulfonyl chloride → (E)-4-(3,4-dichlorophenyl)but-3-enyl methanesulfonate

HRID 1848368ノート

反応式

HRID 1848368 の反応式
[Cl:1][C:2]1[CH:3]=[C:4](/[CH:9]=[CH:10]/[CH2:11][CH2:12][OH:13])[CH:5]=[CH:6][C:7]=1[Cl:8].[CH3:14][S:15](Cl)(=[O:17])=[O:16]>C(Cl)Cl.O>[CH3:14][S:15]([O:13][CH2:12][CH2:11]/[CH:10]=[CH:9]/[C:4]1[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=1)(=[O:17])=[O:16]

参加物

5

反応物 2

HCID 31297Methanesulfonyl chlorideHCID 86728170(E)-4-(3,4-dichlorophenyl)but-3-en-1-ol

生成物 1

HCID 86728171(E)-4-(3,4-dichlorophenyl)but-3-enyl methanesulfonate収率 97%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒2 回

反応条件

温度
0 °C

実験手順

To a solution of Intermediate 2B (986 mg, 4.54 mmol) in CH2Cl2 (20 mL) was added TEA (1.899 mL, 13.63 mmol). The mixture was cooled to 0° C. and methanesulfonyl chloride (0.531 mL, 6.81 mmol) was added dropwise. The reaction was stirred for 45 min at 0° C. then warmed to rt and diluted with water (20 ml) and CH2Cl2 (20 mL). The layers were separated, and the aqueous layer extracted with CH2Cl2. The combined organic extracts were washed with saturated aqueous NaCl, dried over Na2SO4, filtered and concentrated in vacuo to give Intermediate 2C (1.30 g, 97% yield). Intermediate 2C was carried onto the next reaction without further purification. HPLC/MS (Method D) RT=1.10 min, [M-MeSO3H+H]+ 199.1.

後処理

  1. temperaturethen warmed to rt
  2. customThe layers were separated
  3. extractionthe aqueous layer extracted with CH2Cl2
  4. washThe combined organic extracts were washed with saturated aqueous NaCl
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-d9325eed811b432c97d0de94666564c9
出典データセット
uspto-grants-2015_02
特許番号
US08952180B2

反応ノート

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