Isopropanol → 2-Chloro-6-(propan-2-yloxy)pyrazine

HRID 634279노트

반응식

HRID 634279 반응식
[CH3:1][CH:2]([OH:4])[CH3:3].[H-].[Na+].[Cl:7][C:8]1[CH:13]=[N:12][CH:11]=[C:10](Cl)[N:9]=1>C1COCC1>[Cl:7][C:8]1[CH:13]=[N:12][CH:11]=[C:10]([O:4][CH:2]([CH3:3])[CH3:1])[N:9]=1

참가 물질

5

반응물 3

HCID 3776IsopropanolHCID 24758Sodium hydrideHCID 785042,6-Dichloropyrazine

생성물 1

HCID 246891122-Chloro-6-(propan-2-yloxy)pyrazine수율 86.9%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 2-propanol (2.26 mL, 31.99 mmol) in dry THF (40 mL) was added 60% NaH (960 mg, 39.90 mmol) at 0° C. and the reaction was stirred for 15 min. To the mixture at 0° C. was added 2,6-dichloropyrazine (4 g, 26.66 mmol, Aldrich) and the reaction was stirred for 2 h at RT. The reaction was quenched with ice cold H2O (20 mL) and extracted with EtOAc. The organic layer was dried over anhydrous Na2SO4, filtered and concentrated. The residue was purified with silica gel column chromatography (eluent: 100% petroleum ether) to afford 2-chloro-6-isopropoxypyrazine (4.0 g, 86%) as an off brown liquid. MS (ESI, pos. ion) m/z: 173.0 (M+1); 1H NMR (400 MHz, CDCl3): δ 8.28 (s, 1H), 8.14 (s, 1H), 5.31-5.25 (m, 1H), 1.37-1.36 (m, 6H).

후처리

  1. stirringthe reaction was stirred for 2 h at RT
  2. customThe reaction was quenched with ice cold H2O (20 mL)
  3. extractionextracted with EtOAc
  4. dry with materialThe organic layer was dried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified with silica gel column chromatography (eluent: 100% petroleum ether)

출처 및 근거

ORD 기록
ord-725246455299469fa8a19cbbb1b058e6
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09321756B2

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