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Potassium Carbonate → HCID 57545169、化合物

HRID 1661521
ノート
印刷プレビュー

反応式

HRID 1661521 の反応式
[I-].[I-].[Sm+2].[Br:4][C:5]1[CH:10]=[CH:9][C:8]([C@:11]2([C@H:27]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[CH2:28][CH:29]=[O:30])[C:15](=[O:16])[C:14]3[C:17]([O:24][CH2:25][CH3:26])=[CH:18][C:19]([O:21][CH2:22][CH3:23])=[CH:20][C:13]=3[O:12]2)=[CH:7][CH:6]=1.C(=O)([O-])[O-].[K+].[K+]>C1COCC1>[Br:4][C:5]1[CH:10]=[CH:9][C:8]([C@:11]23[C@H:27]([C:31]4[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=4)[CH2:28][C@H:29]([OH:30])[C@@:15]2([OH:16])[C:14]2[C:17]([O:24][CH2:25][CH3:26])=[CH:18][C:19]([O:21][CH2:22][CH3:23])=[CH:20][C:13]=2[O:12]3)=[CH:7][CH:6]=1
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

5

反応物 3

HCID 11430Potassium CarbonateHCID 57545213HCID 57545213、化合物HCID 178506586HCID 178506586、化合物

生成物 1

HCID 57545169HCID 57545169、化合物

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
0 °C

実験手順

178 ml (17.9 mmol) of a 0.1 M solution of samarium diiodide in THF is cooled to 0° C. under argon, and a solution of 2.60 g (5.10 mmol) of (S*,R*)-3-[2-(4-bromophenyl)-4,6-diethoxy-3-oxo-2,3-dihydrobenzofuran-2-yl]-3-phenylpropanal in 30 ml of degassed THF is added dropwise. The mixture is stirred at 0° C. for 1 h and at RT for 1 h. An ice-cold saturated sodium potassium tartrate solution with 10% potassium carbonate is added, the phases are separated, the aqueous phase is extracted three times with dichloromethane, and the combined organic phases are washed with saturated sodium chloride solution, dried over sodium sulfate, filtered and concentrated. Column chromatography on silica gel 60 (mobile phase: toluene/ethyl acetate 95:5) results in 1.55 g (58% of theory) of the product as racemic mixture.

後処理

  1. customthe phases are separated
  2. extractionthe aqueous phase is extracted three times with dichloromethane
  3. washthe combined organic phases are washed with saturated sodium chloride solution
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customColumn chromatography on silica gel 60 (mobile phase: toluene/ethyl acetate 95:5) results in 1.55 g (58% of theory) of the product as racemic mixture

出典と根拠

ORDレコード
ord-a5358a944746455a863d7726f9042285
出典データセット
uspto-grants-2011_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08030347B2

反応ノート

読み込み中…

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