Ammonium Chloride → (2,5-Dichloropyridin-3-yl)(2-fluoro-3-methoxy-6-vinylphenyl)methanol

HRID 222315ノート

反応式

HRID 222315 の反応式
[Li]CCCC.Br[C:7]1[C:8]([Cl:14])=[N:9][CH:10]=[C:11]([Cl:13])[CH:12]=1.[F:15][C:16]1[C:23]([O:24][CH3:25])=[CH:22][CH:21]=[C:20]([CH:26]=[CH2:27])[C:17]=1[CH:18]=[O:19].[NH4+].[Cl-]>C(OC(C)C)(C)C.C1C=CC=CC=1>[Cl:14][C:8]1[C:7]([CH:18]([C:17]2[C:20]([CH:26]=[CH2:27])=[CH:21][CH:22]=[C:23]([O:24][CH3:25])[C:16]=2[F:15])[OH:19])=[CH:12][C:11]([Cl:13])=[CH:10][N:9]=1

参加物

7

反応物 4

HCID 25517Ammonium ChlorideHCID 129015963-Bromo-2,5-dichloropyridineHCID 577227732-Fluoro-3-methoxy-6-vinylbenzaldehydeHCID 178418339Butyllithium

生成物 1

HCID 86609785(2,5-Dichloropyridin-3-yl)(2-fluoro-3-methoxy-6-vinylphenyl)methanol

試薬・触媒・溶媒 2

HCID 241Benzene溶媒HCID 7914Diisopropyl Ether溶媒3 回

反応条件

温度
-78 °C

実験手順

To a stirred solution of nBuLi (1.6 M in hexane, 29.0 mL, 46.4 mmol) in diisopropyl ether (80 mL) was added 3-bromo-2,5-dichloropyridine (10.5 g, 46.4 mmol) in diisopropylether (60 mL) slowly at −78° C. The resulting suspension was treated with 2-fluoro-3-methoxy-6-vinylbenzaldehyde (7.6 g, 42.2 mmol) in diisopropylether (60 mL) and benzene (3 mL), and allowed to stir at −78° C. for 30 min followed by warming to room temperature as the bath did. The mixture was treated with saturated NH4Cl solution and extracted with EtOAc (×3). The combined organics were washed with brine, dried (Na2SO4), concentrated, and purified by flash chromatography to afford the title compound.

後処理

  1. temperatureby warming to room temperature as the bath
  2. extractionextracted with EtOAc (×3)
  3. washThe combined organics were washed with brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. custompurified by flash chromatography

出典と根拠

ORDレコード
ord-b2fb74cdb25045bfaae5b9c74f8539f0
出典データセット
uspto-grants-2012_06
特許番号
US08207186B2

反応ノート

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