N-methyl-2-pyrrolidone → 2-(Benzyloxy)-6-butylpyridine

HRID 909849

반응식

HRID 909849 반응식
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11](Cl)[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN1[CH2:21][CH2:20][CH2:19][C:18]1=O.C([Mg]Br)CCC>O1CCCC1.C/C(/[O-])=C/C(C)=O.C/C(/[O-])=C/C(C)=O.C/C(/[O-])=C/C(C)=O.[Fe+3]>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH2:18][CH2:19][CH2:20][CH3:21])[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

6

반응물 3

HCID 13387N-methyl-2-pyrrolidoneHCID 112644642-(Benzyloxy)-6-chloropyridineHCID 178418682HCID 178418682, 화합물

생성물 1

HCID 666264812-(Benzyloxy)-6-butylpyridine

시약·촉매·용매 2

HCID 5483663Ferric acetylacetonate촉매HCID 8028Tetrahydrofuran용매2회

실험 절차

To a flask were added 2.0 g 2-(benzyloxy)-6-chloropyridine, 5.0 ml 1-methyl-2-pyrrolidinone and 50 ml of dry tetrahydrofuran. After cooling to 5 C under nitrogen, 0.16 g iron(III) acetylacetonate were added followed by drop wise addition of 8.5 ml of a 2M solution of butylmagnesium bromide in tetrahydrofuran. After stirring for 1 hour at 22 C, the reaction was cooled to 10 C and quenched with 20 ml aqueous ammonium chloride. The mixture was diluted with water and extracted with hexane. After washing with water and removal of solvent, the product was purified by silica gel chromatography using 10% ethyl acetate in hexane to give 1.6 g of an oil.

후처리

  1. temperatureAfter cooling to 5 C under nitrogen
  2. temperaturethe reaction was cooled to 10 C
  3. customquenched with 20 ml aqueous ammonium chloride
  4. additionThe mixture was diluted with water
  5. extractionextracted with hexane
  6. washAfter washing with water and removal of solvent
  7. customthe product was purified by silica gel chromatography

출처 및 근거

ORD 기록
ord-97c872be6b04435a8d61bcc2d971664c
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08018639B2

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