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

HRID 1025678노트

반응식

HRID 1025678 반응식
[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

참가 물질

4

반응물 2

HCID 24386Thionyl ChlorideHCID 21187637HCID 21187637, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-26449e8d969b4e3d87a19cebdf1acc30
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08729063B2

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