Thionyl Chloride → 5-(1-Chloroethyl)quinoline

HRID 747272ノート

反応式

HRID 747272 の反応式
[N:1]1[C:10]2[C:5](=[C:6]([CH:11](O)[CH3:12])[CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.S(Cl)([Cl:16])=O>C(Cl)(Cl)Cl>[Cl:16][CH:11]([C:6]1[CH:7]=[CH:8][CH:9]=[C:10]2[C:5]=1[CH:4]=[CH:3][CH:2]=[N:1]2)[CH3:12]

参加物

4

反応物 2

HCID 24386Thionyl ChlorideHCID 687709021-(Quinolin-5-yl)ethanol

生成物 1

HCID 597495555-(1-Chloroethyl)quinoline

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒

反応条件

温度
0 °C

実験手順

The alcohol, 1-quinolin-5-yl-ethanol (5.0 g, 28.9 mmol) in chloroform was treated with a dropwise addition of thionyl chloride (5.26 mL, 72.1 mmol) at rt. After 1 h the mixture was cooled to 0° C. and carefully quenched with a sat. solution of NaHCO3 followed by 2M NaOH until the pH was >8. The aqueous layer was extracted with chloroform and the organic fractions were combined, dried over MgSO4, filtered, and freed of solvent. The residue was purified by chromatography on SiO2 eluting with 30% ethyl acetate:hexane. The product, 5-(1-chloro-ethyl)-quinoline (Intermediate E1) was obtained as a clear oil, 4.22 g (76%).

後処理

  1. customcarefully quenched with a sat. solution of NaHCO3
  2. extractionThe aqueous layer was extracted with chloroform
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customThe residue was purified by chromatography on SiO2 eluting with 30% ethyl acetate

出典と根拠

ORDレコード
ord-8f4aca626f2c4d9b87feb4580cca7524
出典データセット
uspto-grants-2008_07
特許番号
US07396849B2

反応ノート

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