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Allyl bromide → Trans-2-(4-allyloxy-3-methoxy-5-nitrophenyl)-4-(3,4,5-trimethoxyphenyl)-1,3-dithiolane

HRID 260976
ノート
印刷プレビュー

反応式

HRID 260976 の反応式
[OH:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][C:5]([C@H:11]2[S:15][C@H:14]([C:16]3[CH:21]=[C:20]([O:22][CH3:23])[C:19]([O:24][CH3:25])=[C:18]([O:26][CH3:27])[CH:17]=3)[CH2:13][S:12]2)=[CH:4][C:3]=1[O:28][CH3:29].[CH2:30](Br)[CH:31]=[CH2:32].C1OCCOCCOCCOCCOCCOC1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH2:32]([O:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][C:5]([C@H:11]2[S:15][C@H:14]([C:16]3[CH:17]=[C:18]([O:26][CH3:27])[C:19]([O:24][CH3:25])=[C:20]([O:22][CH3:23])[CH:21]=3)[CH2:13][S:12]2)=[CH:4][C:3]=1[O:28][CH3:29])[CH:31]=[CH2:30]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 2855718-Crown-6HCID 86749583trans-2-(4-Hydroxy-3-methoxy-5-nitrophenyl)-4-(3,4,5-trimethoxyphenyl)-1,3-dithiolane

生成物 1

HCID 86749584Trans-2-(4-allyloxy-3-methoxy-5-nitrophenyl)-4-(3,4,5-trimethoxyphenyl)-1,3-dithiolane収率 95%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
50 °C

実験手順

Trans-2-(4-hydroxy-3-methoxy-5-nitrophenyl)-4-(3,4,5-trimethoxy-phenyl)-1,3-dithiolane (21) (2.50 g, 5.69 mmole) was dissolved in 30 ml dry DMF and allyl bromide (0.963 g, 7.97 mmole) was added by syringe. To this solution was added 100 mg of 18-crown-6 and potassium carbonate (0.785 g, 5.69 mmole). The reaction was stirred at 50° C. under an argon atmosphere for 4 hours. The reaction was quenched with 10% HCl and extracted with diethyl ether. The organic layer was dried over MgSO4, and concentrated to a yellow oil in vacuo which was purified by flash column chromatography with 3:1-2:1 hexane/ethyl acetate as eluent. (2.60 g, 95% yield: colorless oil).

後処理

  1. customThe reaction was quenched with 10% HCl
  2. extractionextracted with diethyl ether
  3. dry with materialThe organic layer was dried over MgSO4
  4. concentrationconcentrated to a yellow oil in vacuo which
  5. customwas purified by flash column chromatography with 3:1-2:1 hexane/ethyl acetate as eluent

出典と根拠

ORDレコード
ord-a6cf6e13e1124eca8c395670b9ca4b37
出典データセット
uspto-grants-1996_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05530141

反応ノート

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