Diisopropylamine → 2-Chloro-alpha-(3-methoxyphenyl)-3-pyridinemethanol

HRID 852088

反応式

HRID 852088 の反応式
C([Li])CCC.C(NC(C)C)(C)C.C([N-]C(C)C)(C)C.[Li+].[Cl:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=1.[CH:28](=[O:37])[C:29]1[CH:34]=[CH:33][CH:32]=[C:31]([O:35][CH3:36])[CH:30]=1.[Cl-].[NH4+]>CCCCCC.O1CCCC1.O>[Cl:21][C:22]1[C:27]([CH:28]([C:29]2[CH:34]=[CH:33][CH:32]=[C:31]([O:35][CH3:36])[CH:30]=2)[OH:37])=[CH:26][CH:25]=[CH:24][N:23]=1

参加物

10

反応物 6

HCID 7912DiisopropylamineHCID 79772-ChloropyridineHCID 115693-MethoxybenzaldehydeHCID 25517Ammonium ChlorideHCID 2724682Lithium diisopropylamideHCID 178418339Butyllithium

生成物 1

HCID 201457332-Chloro-alpha-(3-methoxyphenyl)-3-pyridinemethanol収率 51%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒3 回HCID 8058Hexane溶媒

実験手順

Combine 2.5 M n-butyl lithium in hexane (40 mL), diisopropyl amine (14 mL, 0.10 mol) and cold (−68° C.) tetrahydrofuran (250 mL) and stir for 20 minutes, to generate lithium diisopropylamide. Add 2-chloro-pyridine (9.5 mL, 0.10 mol) dissolved in tetrahydrofuran (10 mL) and stir for 45 minutes. Add m-anisaldehyde (13.6 g, 0.10 mol) in 10 mL tetrahydrofuran, stir for 45 minutes and let warm to room temperature over the weekend. Pour reaction mixture into water, add saturated ammonium chloride (50 mL), separate and dry. Extract with ether (twice), wash combined aqueous layers with saturated sodium chloride, dry, evaporate and purify by flash (silica) chromatography using a graded solvent mixture of dichloromethane to 10% ethyl acetate in dichloromethane to give the title compound as an oil (12.74 g, 51% Yield). NMR agrees with the final, desired compound.

後処理

  1. additionPour
  2. customseparate
  3. customdry
  4. extractionExtract with ether (twice),
  5. washwash
  6. customdry
  7. customevaporate
  8. custompurify by flash (silica) chromatography
  9. additiona graded solvent mixture of dichloromethane to 10% ethyl acetate in dichloromethane

出典と根拠

ORDレコード
ord-0b4136e69fa14d5aabb9d73c5cf3a4d0
出典データセット
uspto-grants-2007_08
特許番号
US07253165B2

関連ノート

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