2-Bromo-6-(1,3-dioxolan-2-yl)pyridine → HCID 89853573, 화합물

HRID 931087노트

반응식

HRID 931087 반응식
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH:8]2[O:12][CH2:11][CH2:10][O:9]2)[N:3]=1.C([Li])CCC.[O:18]1[CH2:21][C:20](=[O:22])[CH2:19]1>O1CCCC1>[O:9]1[CH2:10][CH2:11][O:12][CH:8]1[C:4]1[N:3]=[C:2]([C:20]2([OH:22])[CH2:21][O:18][CH2:19]2)[CH:7]=[CH:6][CH:5]=1

참가 물질

5

반응물 3

HCID 1186132-Bromo-6-(1,3-dioxolan-2-yl)pyridineHCID 150242543-OxetanoneHCID 178418339Butyllithium

생성물 1

HCID 89853573HCID 89853573, 화합물수율 27%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

To a solution of 2-bromo-6-(1,3-dioxolan-2-yl)pyridine (2.49 g, 10.8 mmol) in anhydrous tetrahydrofuran (40 mL) was added a solution of n-butyllithium (2.5 M, 4.3 mL, 10.8 mmol) at −78° C. After stirring for 30 min., a solution of oxetan-3-one (0.6 g, 8.32 mmol) in anhydrous tetrahydrofuran (12 mL) was added slowly and the mixture was stirred at that temperature for 1 h. The reaction mixture was quenched with water and extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate, filtered and concentrated under reduced pressure to afford the crude compound. The crude material was purified via preparative TLC eluting with 35% ethyl acetate in petroleum ether to afford 3-(6-(1,3-dioxolan-2-yl)pyridin-2-yl)oxetan-3-ol (500 mg, 27%). MS (ES+) (M+H) 224.20; LCMS retention time: 2.76 minutes (Method S).

후처리

  1. stirringthe mixture was stirred at that temperature for 1 h
  2. customThe reaction mixture was quenched with water
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customto afford the crude compound
  9. customThe crude material was purified via preparative TLC
  10. washeluting with 35% ethyl acetate in petroleum ether

출처 및 근거

ORD 기록
ord-8e1ba8432d604ab0a3ab620def49ed29
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09296745B2

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