Water → 2,5-Dichloro-pyridine-3-carbaldehyde

HRID 11680

反応式

HRID 11680 の反応式
[Cl:1][C:2]1[N:10]=[CH:9][C:8]([Cl:11])=[CH:7][C:3]=1[C:4](Cl)=[O:5].C([SnH](CCCC)CCCC)CCC.O>O1CCCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:1][C:2]1[C:3]([CH:4]=[O:5])=[CH:7][C:8]([Cl:11])=[CH:9][N:10]=1

参加物

6

反応物 3

HCID 962WaterHCID 5948TributylstannaneHCID 27999962,5-Dichloro-nicotinoyl chloride

生成物 1

HCID 219732742,5-Dichloro-pyridine-3-carbaldehyde収率 34.4%

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 2,5-Dichloro-nicotinoyl chloride (15 g, 0.071 mol) in tetrahydrofuran was added tributyl-stannane (24.9 g, 0.086 mol) portionwise over 45 minutes. The resulting mixture was stirred at ambient temperature for 50 minutes, and then treated with tetrakis(triphenylphosphine)palladium(0) (0.82 g, 0.00071 mol). The reaction mixture was stirred at ambient temperature for 4 hours, poured into water; the product was extracted with ethylacetate, the combined organics were dried over magnesium sulfate, filtered and concentrated in vacuo. Silica gel chromatography (10% ethyl acetate/hexanes) followed by recrystallization from hexanes/ethylacetate gave the title compound (4.3 g).

後処理

  1. stirringThe reaction mixture was stirred at ambient temperature for 4 hours
  2. extractionthe product was extracted with ethylacetate
  3. dry with materialthe combined organics were dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customSilica gel chromatography (10% ethyl acetate/hexanes) followed by recrystallization from hexanes/ethylacetate

出典と根拠

ORDレコード
ord-38c6d934eb854ee7a469257bfdad0650
出典データセット
uspto-grants-2006_08
特許番号
US07098212B2

関連ノート

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