1,10-Phenanthroline → 2-[(1-Hydroxy-1-methylpropyl)]-1,10-phenanthroline

HRID 1581751ノート

反応式

HRID 1581751 の反応式
[N:1]1[C:14]2[C:5](=[CH:6][CH:7]=[C:8]3[C:13]=2[N:12]=[CH:11][CH:10]=[CH:9]3)[CH:4]=[CH:3][CH:2]=1.[I-].[I-].[Sm+2].[CH2:18]([C:20]([CH3:22])=[O:21])[CH3:19]>O1CCCC1>[OH:21][C:20]([C:2]1[CH:3]=[CH:4][C:5]2[C:14](=[C:13]3[C:8](=[CH:7][CH:6]=2)[CH:9]=[CH:10][CH:11]=[N:12]3)[N:1]=1)([CH3:22])[CH2:18][CH3:19]

参加物

5

反応物 3

HCID 13181,10-PhenanthrolineHCID 6569Methyl Ethyl KetoneHCID 178506586HCID 178506586、化合物

生成物 1

HCID 104223302-[(1-Hydroxy-1-methylpropyl)]-1,10-phenanthroline

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
25 °C

実験手順

An embodiment of the process comprises mixing a stirred solution of 1,10-phenanthroline in tetrahydrofuran (THF) with a solution of the lanthanideII, samarium diiodide, in THF at a temperature of about 25° C. To the mixed solutions is added a solution of the ketone, methyl ethyl ketone, and the reaction mixture is stirred at about 25° C. for about 12 hours. The reaction is then quenched by the addition of a saturated aqueous solution of ammonium chloride and the mixture extracted with methylene chloride. The extract is washed with brine, dried and concentrated in vacao. The concentrate of product is purified by flash chromatography using alumina and ethyl acetate-hexanes as a gradient to provide racemic 2-[(1-hydroxy-1-methylpropyl)]-1,10-phenanthroline. (Formula 1, R=H, R1=ethyl, R2=methyl) This embodiment is depicted in the following reaction scheme wherein MEK is methyl ethyl ketone.

後処理

  1. customat a temperature of about 25° C
  2. customThe reaction is then quenched by the addition of a saturated aqueous solution of ammonium chloride
  3. extractionthe mixture extracted with methylene chloride
  4. washThe extract is washed with brine
  5. customdried
  6. concentrationconcentrated in vacao
  7. concentrationThe concentrate of product
  8. customis purified by flash chromatography

出典と根拠

ORDレコード
ord-5beac8eeb5d94f9496ac71b6a127be55
出典データセット
uspto-grants-2004_05
特許番号
US06730788B1

反応ノート

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