Pivalaldehyde → HCID 22009516、化合物

HRID 322030ノート

反応式

HRID 322030 の反応式
Br[C:2]1[CH:3]=[C:4]([CH3:9])[C:5]([F:8])=[N:6][CH:7]=1.C([Li])CCC.CC(C)(C)[CH:17]=[O:18]>CCOCC>[F:8][C:5]1[N:6]=[CH:7][C:2]([CH2:17][OH:18])=[CH:3][C:4]=1[CH3:9]

参加物

5

反応物 3

HCID 12417PivalaldehydeHCID 120569025-Bromo-2-fluoro-3-methylpyridineHCID 178418339Butyllithium

生成物 1

HCID 22009516HCID 22009516、化合物収率 103.1%

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

反応条件

温度
-70 °C

実験手順

5-Bromo-2-fluoro-3-methylpyridine (2.0 g, 0.011 mol) was dissolved with stirring in anhydrous ether (30 mL) and cooled to −70° C. This was treated at <−60° C. with n-butyl lithium (4.8 mL, 2.5M in hexane, 0.012 mol) and the reaction mixture stirred at <−70° C. for one hour. Trimethylacetaldehyde (1.14 g, 0.013 mol) was added and the reaction mixture allowed to warm to −10° C. The reaction mixture was quenched with ammonium chloride solution and extracted with ethyl acetate. The organic extract was washed with water and brine, dried (Na2SO4) and evaporated to dryness. Purification of the residue by chromatography over silica (5-25% ethyl acetate:hexane) gave the desired product (1.6 g, 77%) as a clear oil.

後処理

  1. temperatureto warm to −10° C
  2. customThe reaction mixture was quenched with ammonium chloride solution
  3. extractionextracted with ethyl acetate
  4. extractionThe organic extract
  5. washwas washed with water and brine
  6. dry with materialdried (Na2SO4)
  7. customevaporated to dryness
  8. customPurification of the residue by chromatography over silica (5-25% ethyl acetate:hexane)

出典と根拠

ORDレコード
ord-33185891b54946c7a2bc831739e70285
出典データセット
uspto-grants-2001_04
特許番号
US06211202B1

反応ノート

読み込み中…