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

HRID 909849

反応式

HRID 909849 の反応式
[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

参加物

6

反応物 3

HCID 13387N-methyl-2-pyrrolidoneHCID 112644642-(Benzyloxy)-6-chloropyridineHCID 178418682HCID 178418682、化合物

生成物 1

HCID 666264812-(Benzyloxy)-6-butylpyridine

試薬・触媒・溶媒 2

HCID 5483663Ferric acetylacetonate触媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-97c872be6b04435a8d61bcc2d971664c
出典データセット
uspto-grants-2011_09
特許番号
US08018639B2

関連ノート

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