Thionyl Chloride → 4-(1-Chloroethyl)quinoline

HRID 1597364ノート

反応式

HRID 1597364 の反応式
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([CH:11](O)[CH3:12])=[CH:3][CH:2]=1.S(Cl)([Cl:16])=O>C(Cl)(Cl)Cl>[Cl:16][CH:11]([C:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[N:1]=[CH:2][CH:3]=1)[CH3:12]

参加物

4

反応物 2

HCID 24386Thionyl ChlorideHCID 53147551-(Quinolin-4-yl)ethanol

生成物 1

HCID 141713954-(1-Chloroethyl)quinoline収率 100%

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒

反応条件

温度
0 °C

実験手順

To 1-Quinolin-4-yl-ethanol (1.4 g, 8.09 mmol) in 15 ml chloroform, thiony-chloride (1.8 ml, 20.2 mmol) was added dropwise over a five minute period at room temperature. Stirring was continued for 30 minutes after which the reaction mixture was cooled to 0° C. and quenched carefully by the addition of saturated aqueous NaHCO3 (20 ml). The chloroform layer was dried over sodium sulfate, filtered and concentrated. Column purification (hexane:ethyl acetate; 1.5:3.5) gave 1.54 g (100%) of the product as a syrup which was used as such for the subsequent step.

後処理

  1. customquenched carefully by the addition of saturated aqueous NaHCO3 (20 ml)
  2. dry with materialThe chloroform layer was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customColumn purification (hexane:ethyl acetate; 1.5:3.5)

出典と根拠

ORDレコード
ord-1483d4265d4e4d3298d7d1030a129870
出典データセット
uspto-grants-2001_09
特許番号
US06294566B1

反応ノート

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