Water → Methyl 2-(2-(3-(3-(2-(7-chloro-2-quinolinyl)ethenyl)phenyl)-3-oxopropyl)phenyl)propanoate

HRID 865468ノート

反応式

HRID 865468 の反応式
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([CH:12]=[CH:13][C:14]3[CH:15]=[C:16]([CH:20]([OH:23])[CH:21]=[CH2:22])[CH:17]=[CH:18][CH:19]=3)=[N:9]2)=[CH:4][CH:3]=1.[Li]OC(C)=O.O.[Li+].[Cl-].I[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=1[CH:39]([CH3:44])[C:40]([O:42][CH3:43])=[O:41].C([O-])(O)=O.[Na+]>[N+](CCCC)(CCCC)(CCCC)CCCC.[Cl-].CN(C=O)C.CC([O-])=O.CC([O-])=O.[Pd+2]>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([CH:12]=[CH:13][C:14]3[CH:15]=[C:16]([C:20](=[O:23])[CH2:21][CH2:22][C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=4[CH:39]([CH3:44])[C:40]([O:42][CH3:43])=[O:41])[CH:17]=[CH:18][CH:19]=3)=[N:9]2)=[CH:4][CH:3]=1

参加物

10

反応物 6

HCID 962WaterHCID 433294Lithium ChlorideHCID 516892Sodium BicarbonateHCID 534062851-(3-(2-(7-Chloro-2-quinolinyl)ethenyl)phenyl)-2-propen-1-olHCID 54386704Methyl 2-iodo-alpha-methylbenzeneacetateHCID 178506943lithium acetate

生成物 1

HCID 53934601Methyl 2-(2-(3-(3-(2-(7-chloro-2-quinolinyl)ethenyl)phenyl)-3-oxopropyl)phenyl)propanoate

試薬・触媒・溶媒 3

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

反応条件

温度
0 °C

実験手順

A degassed suspension of the product of Step 1 (15.0 g, 46.6 mmol), n-Bu4NCl (25.9 g, 93 mmol), LiOAc.circle-solid.H2O (7.7 g, 115 mmol), LiCl (1.98 g, 93 mmol), Pd(OAc)2 (0.315 g, 1.4 mmol), and methyl 2-(2-iodophenyl)propanoate in DMF (90 mL) was stirred for 2 hours at 100° C. The dark red solution was then cooled to 0° C. and poured into saturated NaHCO3 solution (500 mL). The product was extracted with EtOAc and the organic layer was washed with H2O followed by brine. The solvent was removed under vacuum and the residue was purified by flash chromatography (EtOAc:hexane 1:10, 1:5 and 3:10) to give a pale yellow foam (18.9 g).

後処理

  1. extractionThe product was extracted with EtOAc
  2. washthe organic layer was washed with H2O
  3. customThe solvent was removed under vacuum
  4. customthe residue was purified by flash chromatography (EtOAc:hexane 1:10, 1:5 and 3:10)

出典と根拠

ORDレコード
ord-b4765b3a5b4948698196192a1cf62365
出典データセット
uspto-grants-1996_10
特許番号
US05565473

反応ノート

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