Pivalaldehyde → HCID 22009516, 화합물

HRID 322030노트

반응식

HRID 322030 반응식
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]

참가 물질

5

반응물 3

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

생성물 1

HCID 22009516HCID 22009516, 화합물수율 103.1%

시약·촉매·용매 1

HCID 3283Diethyl Ether용매

반응 조건

온도
-70 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-33185891b54946c7a2bc831739e70285
출처 데이터셋
uspto-grants-2001_04
특허 번호
US06211202B1

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