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Iodoethylene → (1RS,2SR,6RS,7SR,8RS)-4-(2,4,6-trimethylphenyl)-8-vinyl-10-oxatricyclo[5.2.1.02,6]decane-3,5-dione

HRID 407860
ノート
印刷プレビュー

反応式

HRID 407860 の反応式
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[C:3]=1[CH:10]1[C:18](=[O:19])[CH:17]2[CH:12]([CH:13]3[O:20][CH:16]2[CH:15]=[CH:14]3)[C:11]1=[O:21].[CH:22](I)=[CH2:23].C([O-])=O.[Na+]>[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C)C=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[C:3]=1[CH:10]1[C:11](=[O:21])[CH:12]2[CH:17]([CH:16]3[O:20][CH:13]2[CH:14]([CH:22]=[CH2:23])[CH2:15]3)[C:18]1=[O:19]
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

7

反応物 3

HCID 68976IodoethyleneHCID 2723810Sodium FormateHCID 67283862(1RS,2SR,6RS,7SR)-4-(2,4,6-trimethylphenyl)-10-oxatricyclo-[5.2.1.02,6]dec-8-en-3,5-dione

生成物 1

HCID 67284357(1RS,2SR,6RS,7SR,8RS)-4-(2,4,6-trimethylphenyl)-8-vinyl-10-oxatricyclo[5.2.1.02,6]decane-3,5-dione

試薬・触媒・溶媒 3

HCID 70681Tetrabutylammonium Chloride触媒
HCID 167845
palladium(II) acetate
触媒
HCID 6228Dimethylformamide溶媒

反応条件

温度
150 °C

実験手順

A mixture of (1RS,2SR,6RS,7SR)-4-(2,4,6-trimethylphenyl)-10-oxatricyclo[5.2.1.02,6]dec-8-en-3,5-dione (510 mg, 1.8 mmol), vinyl iodide (280 mg, 1.8 mmol), palladium acetate (20 mg, 0.09 mmol), sodium formate (454 mg, 5.4 mmol) and tetrabuylammonium chloride (500 mg, 1.8 mmol) in dry N,N-dimethylformamide (15 ml) are heated at 150° C. for 20 minutes under microwave irradiation. The mixture is cooled to room temperature and partitioned between water and ethyl acetate. The organic extracts are combined, dried over anhydrous magnesium sulfate, filtered and the filtrate is evaporated under reduced pressure. The residue is purified by column chromatography on silica gel to give (1RS,2SR,6RS,7SR,8RS)-4-(2,4,6-trimethylphenyl)-8-vinyl-10-oxatricyclo[5.2.1.02,6]decane-3,5-dione.

後処理

  1. temperatureThe mixture is cooled to room temperature
  2. custompartitioned between water and ethyl acetate
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customthe filtrate is evaporated under reduced pressure
  6. customThe residue is purified by column chromatography on silica gel

出典と根拠

ORDレコード
ord-e1d8629c5767441d96d9519e3d5c70bf
出典データセット
uspto-grants-2014_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08754242B2

反応ノート

読み込み中…

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