Methyl anisate → 2-(4-Bromopyridin-2-yl)-1-(4-methoxyphenyl)ethanone

HRID 705374

反応式

HRID 705374 の反応式
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9]C)=O)=[CH:5][CH:4]=1.[Br:13][C:14]1[CH:19]=[CH:18][N:17]=[C:16]([CH3:20])[CH:15]=1.C[Si](C)(C)[N-][Si](C)(C)C.[Li+]>O1CCCC1>[Br:13][C:14]1[CH:19]=[CH:18][N:17]=[C:16]([CH2:20][C:7]([C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:12][CH:11]=2)=[O:9])[CH:15]=1

参加物

5

反応物 3

HCID 8499Methyl anisateHCID 2733832Lithium HexamethyldisilazideHCID 27628354-Bromo-2-methylpyridine

生成物 1

HCID 682760292-(4-Bromopyridin-2-yl)-1-(4-methoxyphenyl)ethanone収率 88%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

In a 250 mL round-bottomed flask at 0° C. under nitrogen was added methyl 4-methoxybenzoate (Aldrich, 3.32 g, 20.00 mmol) and 4-bromo-2-methylpyridine (Frontier, 1.72 g, 10.00 mmol) in anhydrous tetrahydrofuran (40.0 mL) to give a yellow solution. Lithium hexamethyldisilazide (1 M in tetrahydrofuran, 20 mL, 20 mmol) was added dropwise over 15 minutes via a dropping addition funnel to produce an orange transparent solution that was stirred for 18 hours at ambient temperature. The mixture was partitioned between ethyl acetate and water. The organic layer was washed with brine, dried (Na2SO4), filtered and concentrated to a reddish oil. Purification by flash chromatography on a silica 80 g cartridge eluting with 10-60% ethyl acetate in hexane gave the title compound (2.68 g, 88%). MS (APCI+) m/z 306/308 (M+H)+.

後処理

  1. customto give a yellow solution
  2. customto produce an orange transparent solution
  3. customThe mixture was partitioned between ethyl acetate and water
  4. washThe organic layer was washed with brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated to a reddish oil
  8. customPurification by flash chromatography on a silica 80 g cartridge
  9. washeluting with 10-60% ethyl acetate in hexane

出典と根拠

ORDレコード
ord-ca36262ee1744184be594846055512b7
出典データセット
uspto-grants-2015_11
特許番号
US09173887B2

関連ノート

読み込み中…