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Chloroform → HCID 57781097、化合物

HRID 1690717
ノート
印刷プレビュー

反応式

HRID 1690717 の反応式
I[C:2]1[N:6]([CH:7]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10](=[O:17])[O:9][C:8]2([CH3:19])[CH3:18])[CH:5]=[N:4][CH:3]=1.[CH2:20](C([Sn])=C(CCCC)CCCC)[CH2:21]CC.C(Cl)(Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(OC(C)C)(=O)C.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].CN(C=O)C>[CH:20]([C:2]1[N:6]([CH:7]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10](=[O:17])[O:9][C:8]2([CH3:19])[CH3:18])[CH:5]=[N:4][CH:3]=1)=[CH2:21]
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

8

反応物 4

HCID 6212ChloroformHCID 11776TriphenylphosphineHCID 53438229Tri(butyl)vinyltinHCID 57781136HCID 57781136、化合物

生成物 1

HCID 57781097HCID 57781097、化合物

試薬・触媒・溶媒 3

HCID 9811564Bis(dibenzylideneacetone)palladium触媒
HCID 6228Dimethylformamide溶媒
HCID 7915Isopropyl Acetate溶媒

反応条件

温度
90 °C

実験手順

DMF (30 mL) is added to 4-(5-iodo-imidazol-1-yl)-3,3-dimethyl-isochroman-1-one (1.62 g, 4.18 mmol) (Example 2b), tributylvinyltin (2.40 g, 8.36 mmol), Pd2 dba3.CHCl3 (0.087 g, 0.084 mmol) and triphenylphosphine (0.089 g, 0.334 mmol) under nitrogen. The mixture is heated to 90° C., to give a clear tan solution. After 3 h, the mixture is cooled down, diluted with isopropyl acetate and washed twice with water and brine. The combined organic phase is dried over magnesium sulfate and filtered through a cotton plug. The residue is purified by silica gel flash chromatography (10% wt silica gel/KF, elution with dichloromethane-methanol, 49:1 to 24:1) to give 4-(5-vinyl-imidazol-1-yl)-3,3-dimethyl-isochroman-1-one as a yellow solid; MS (ESI) m/z 269.2 (M+H); 1H NMR (400 MHz, MeOD) δ ppm 1.20 (s, 3 H), 1.51 (s, 3 H), 5.42 (br. s, 1 H), 5.69 (s, 1 H), 5.81 (br. s, 1 H), 6.95 (br. s, 1 H), 7.14 (br. s, 1H), 7.21 (s, 1 H), 7.42 (d, J=7.6 Hz, 1 H), 7.58-7.69 (m, 1 H), 7.70-7.80 (m, 1 H), 8.21 (dd, J=7.8, 1.3 Hz, 1 H).

後処理

  1. customto give a clear tan solution
  2. temperaturethe mixture is cooled down
  3. washwashed twice with water and brine
  4. dry with materialThe combined organic phase is dried over magnesium sulfate
  5. filtrationfiltered through a cotton plug
  6. customThe residue is purified by silica gel flash chromatography (10% wt silica gel/KF, elution with dichloromethane-methanol, 49:1 to 24:1)

出典と根拠

ORDレコード
ord-3a17397656f849f08f2ad6b97fa02c64
出典データセット
uspto-grants-2012_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08153674B2

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート