Thionyl Chloride → 2-(1,4-Dioxaspiro[4.5]dec-7-en-8-yl)pyridine

HRID 1809841ノート

反応式

HRID 1809841 の反応式
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1(O)[CH2:16][CH2:15][C:10]2([O:14][CH2:13][CH2:12][O:11]2)[CH2:9][CH2:8]1.O=S(Cl)Cl>N1C=CC=CC=1>[O:14]1[C:10]2([CH2:15][CH2:16][C:7]([C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=3)=[CH:8][CH2:9]2)[O:11][CH2:12][CH2:13]1

参加物

4

反応物 2

HCID 24386Thionyl ChlorideHCID 21187637HCID 21187637、化合物

生成物 1

HCID 211876502-(1,4-Dioxaspiro[4.5]dec-7-en-8-yl)pyridine収率 83.4%

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

The ketal (2 g, 8.5 mmol) obtained from step A, Example 7 was dissolved in pyridine (40 mL) and the solution was cooled in an ice bath. To it was added SOCl2 (3.1 mL, 42.5 mmol). The solution was allowed to warm to room temperature and stirring was continued overnight. The reaction was quenched by addition of ice and then water. The resulting solution was extracted with EtOAc three times. The combined EtOAc layer was dried over MgSO4 and concentrated. Flash chromatography on silica gel eluting with 0 to 55% EtOAc/hexanes provided 1.54 g of the title compound. MS calculated (M+H)+218. Found 218.

後処理

  1. temperaturethe solution was cooled in an ice bath
  2. customThe reaction was quenched by addition of ice
  3. extractionThe resulting solution was extracted with EtOAc three times
  4. dry with materialThe combined EtOAc layer was dried over MgSO4
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-ea05eb4430dd4e96a0756b226dd7e135
出典データセット
uspto-grants-2013_01
特許番号
US08362003B2

反応ノート

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