Cyclobutanol → 4-(5-Chloro-2-methoxyphenyl)-2-(cyclobutyloxy)pyridine

HRID 46383노트

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HRID 46383 반응식
Cl[C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[C:12]([Cl:14])[CH:11]=[CH:10][C:9]=2[O:15][CH3:16])[CH:5]=[CH:4][N:3]=1.[CH:17]1([OH:21])[CH2:20][CH2:19][CH2:18]1.CC(C)([O-])C.[K+]>O1CCOCC1>[Cl:14][C:12]1[CH:11]=[CH:10][C:9]([O:15][CH3:16])=[C:8]([C:6]2[CH:5]=[CH:4][N:3]=[C:2]([O:21][CH:17]3[CH2:20][CH2:19][CH2:18]3)[CH:7]=2)[CH:13]=1

참가 물질

5

반응물 3

HCID 76218CyclobutanolHCID 23665647Potassium tert-butoxideHCID 594364732-Chloro-4-(5-chloro-2-methoxyphenyl)pyridine

생성물 1

HCID 594365824-(5-Chloro-2-methoxyphenyl)-2-(cyclobutyloxy)pyridine수율 114.1%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

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온도
101 °C

실험 절차

2-Chloro-4-(5-chloro-2-methoxyphenyl)pyridine (Preparation 864, 150 mg, 0.00059 mol) and cyclobutanol (76.6 mg, 0.00106 mol) were dissolved in 1,4-dioxane (2 mL). Potassium tert-butoxide (132 mg, 0.00118 mol) was added and the solution stirred at 101° C. for 15 hours. The reaction was partitioned between ethyl acetate (15 mL) and a 10% aqueous solution of citric acid (10 mL). The organic layer was washed with water (10 mL) followed by a saturated aqueous sodium chloride solution (10 mL). The organics were dried over anhydrous magnesium sulphate, filtered and the solvents removed in vacuo to give a yellow oil (195 mg). The material was purified using an ISCO™ companion (12 g column, eluting with 100% heptane to 7:3 heptane/ethyl acetate). Fractions containing product were combined and concentrated in vacuo to obtain the title compound as a colourless oil (84 mg).

후처리

  1. customThe reaction was partitioned between ethyl acetate (15 mL)
  2. washThe organic layer was washed with water (10 mL)
  3. dry with materialThe organics were dried over anhydrous magnesium sulphate
  4. filtrationfiltered
  5. customthe solvents removed in vacuo

출처 및 근거

ORD 기록
ord-e3bba557739f48d0932d39d44ee1c412
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08541588B2

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