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

HRID 634279ノート

反応式

HRID 634279 の反応式
[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

参加物

5

反応物 3

HCID 3776IsopropanolHCID 24758Sodium hydrideHCID 785042,6-Dichloropyrazine

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-725246455299469fa8a19cbbb1b058e6
出典データセット
uspto-grants-2016_04
特許番号
US09321756B2

反応ノート

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