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

HRID 1581751노트

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HRID 1581751 반응식
[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]

참가 물질

5

반응물 3

HCID 13181,10-PhenanthrolineHCID 6569Methyl Ethyl KetoneHCID 178506586HCID 178506586, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

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온도
25 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-5beac8eeb5d94f9496ac71b6a127be55
출처 데이터셋
uspto-grants-2004_05
특허 번호
US06730788B1

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