Water → HCID 178489287、化合物

HRID 45429

反応式

HRID 45429 の反応式
Br[C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4](/[C:9](=[N:11]/[C:12]2[C:17]([CH:18]([CH3:20])[CH3:19])=[CH:16][CH:15]=[CH:14][C:13]=2[CH:21]([CH3:23])[CH3:22])/[CH3:10])[C:3]=1[OH:24].[Li]CCCC.Br[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=1[O:37][CH3:38].O>C1COCC1.[Cl-].[Cl-].[Zn+2].CC(C)([P](C(C)(C)C)([Pd][P](C(C)(C)C)(C(C)(C)C)C(C)(C)C)C(C)(C)C)C>[CH:21]([C:13]1[CH:14]=[CH:15][CH:16]=[C:17]([CH:18]([CH3:20])[CH3:19])[C:12]=1/[N:11]=[C:9](/[C:4]1[CH:5]=[C:6]([CH3:8])[CH:7]=[C:2]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=2[O:37][CH3:38])[C:3]=1[OH:24])\[CH3:10])([CH3:23])[CH3:22]

参加物

8

反応物 4

HCID 962WaterHCID 113582-BromoanisoleHCID 178418339ButyllithiumHCID 178463285HCID 178463285、化合物

生成物 1

HCID 178489287HCID 178489287、化合物収率 30%

試薬・触媒・溶媒 3

HCID 3007855Zincchloride触媒HCID 178418851HCID 178418851、化合物触媒HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-100 °C

実験手順

To a solution of 1.94 g (5.0 mmol) of 30 in 20 mL of THF, 4.0 mL (10.0 mmol) of 2.5 M nBuLi in hexanes was added at −80° C. This mixture was stirred at this temperature for 1 hr, then cooled to −100° C., and 10.8 mL (10.8 mmol) of 1.0 M ZnCl2 in THF was added. The resulting mixture was slowly warmed to ambient temperature, stirred for 30 min, and then 2.82 g (15.0 mmol) of 2-bromoanisole and 0.14 g (0.25 mmol) of Pd(PtBu3)2 was added. This mixture was refluxed for 8 hr, then 5 mL of water was added. The resulting mixture was passed through short layer of silica gel 60. The silica gel layer was additionally washed with 30 mL of dichloromethane. The combined organic elute was evaporated to dryness. The product was isolated by flash chromatography on silica gel 60 (40-63 um, eluent: from hexanes to hexanes-ether, 20:1, vol.) to give 0.62 g (30%) of yellowish solid.

後処理

  1. temperatureThe resulting mixture was slowly warmed to ambient temperature
  2. stirringstirred for 30 min
  3. temperatureThis mixture was refluxed for 8 hr
  4. washThe silica gel layer was additionally washed with 30 mL of dichloromethane
  5. washThe combined organic elute
  6. customwas evaporated to dryness
  7. customThe product was isolated by flash chromatography on silica gel 60 (40-63 um, eluent: from hexanes to hexanes-ether, 20:1, vol.)

出典と根拠

ORDレコード
ord-43fab9aeb4764170bff78fec8f872540
出典データセット
uspto-grants-2013_09
特許番号
US08541521B2

関連ノート

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