Ethyl Acetate → HCID 18799859、化合物

HRID 1637767

反応式

HRID 1637767 の反応式
[Cl:1][C:2]1[C:7]([OH:8])=[C:6](I)[CH:5]=[C:4]([CH:10]([OH:12])[CH3:11])[N:3]=1.[CH:13]([Sn](C=C)(C=C)C=C)=[CH2:14].C(OCC)(=O)C>CN(C)C=O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Cl:1][C:2]1[C:7]([OH:8])=[C:6]([CH:13]=[CH2:14])[CH:5]=[C:4]([CH:10]([OH:12])[CH3:11])[N:3]=1

参加物

6

反応物 3

HCID 8857Ethyl AcetateHCID 66189TetravinylstannaneHCID 107092992-Chloro-3-hydroxy-4-iodo-6-(1-hydroxyethyl)-pyridine

生成物 1

HCID 18799859HCID 18799859、化合物収率 70.1%

試薬・触媒・溶媒 2

HCID 178418476HCID 178418476、化合物触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
50 °C

実験手順

A solution of 2-chloro-3-hydroxy-4-iodo-6-(1-hydroxyethyl)-pyridine (3.6 g, 12 mmol) in 36 mL of N,N-dimethylformamide is treated with bis(triphenylphosphine)-palladium dichloride (632 mg, 0.9 mmol) and tetravinyltin (2.7 mL, 15 mmol) and heated at 50° C. for 24 h and at room temperature for 40 h. The mixture is poured into 300 mL of ethyl acetate, filtered through a celite pad and the filtrate is washed with 4×50 mL of saturated sodium chloride. The organics are concentrated in vacuo and the crude material is chromatographed over 150 g of silica gel (230-400 mesh), eluting with 25% ethyl acetate/hexanes to provide 1.68 g (70%) of 2-chloro-3-hydroxy-4-vinyl-6-(1-hydroxyethyl)-pyridine.

後処理

  1. filtrationfiltered through a celite pad
  2. washthe filtrate is washed with 4×50 mL of saturated sodium chloride
  3. concentrationThe organics are concentrated in vacuo
  4. customthe crude material is chromatographed over 150 g of silica gel (230-400 mesh)
  5. washeluting with 25% ethyl acetate/hexanes

出典と根拠

ORDレコード
ord-435c71bc7d3e44518e67d6e4f4da8325
出典データセット
uspto-grants-2000_03
特許番号
US06043248

関連ノート

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