Methyl iodide → 4-(tert-Butoxy)-2,3,6-trifluoro-5-methylpyridine

HRID 1600996

反応式

HRID 1600996 の反応式
[CH2:1]([N-]CC)C.[Li+].[C:7]([O:11][C:12]1[CH:17]=[C:16]([F:18])[N:15]=[C:14]([F:19])[C:13]=1[F:20])([CH3:10])([CH3:9])[CH3:8].CI>C1COCC1>[C:7]([O:11][C:12]1[C:17]([CH3:1])=[C:16]([F:18])[N:15]=[C:14]([F:19])[C:13]=1[F:20])([CH3:10])([CH3:8])[CH3:9]

参加物

5

反応物 3

HCID 6328Methyl iodideHCID 106085474-t-Butoxy-2,3,6-trifluoropyridineHCID 11137085Lithium diethylamide

生成物 1

HCID 107513394-(tert-Butoxy)-2,3,6-trifluoro-5-methylpyridine

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

A freshly prepared solution of lithium diethylamide (LDA) (58.21 mmol) in 30 mL of THF at -78° C. was added to 10.0 g (48.74 mmol) of 4-t-butoxy-2,3,6-trifluoropyridine in 50 mL of THF at -78° C, and the reaction was stirred for 50 min. To the reaction mixture was added 4.3 mL (69.07 mmol) of methyl iodide, and the mixture was stirred at -78° C. for 1 hour and stirred at ambient temperature for 16 hours. The reaction was quenched with saturated NH4Cl solution, extracted with hexane, and the extracts washed with water, dried over MgSO4 and concentrated to give 4-t-butoxy-2,3,6-trifluoro-5-methylpyridine as a pale yellow oil, which was taken directly to the next step. MS (220) (M+H)+ ; 1H NMR (CDCl3)∂: 1.47 (m, 9H), 2.12 (m, 3H). 19F NMR (CDCl3, CFCl3 as reference)∂: 75.91 (dd apparent, J1 =15.0, J2 =22.1 Hz), 93.17 (dd apparent, J1 =15.0, J2 =22.1 Hz), 156.54 (m).

後処理

  1. stirringthe mixture was stirred at -78° C. for 1 hour
  2. stirringstirred at ambient temperature for 16 hours
  3. customThe reaction was quenched with saturated NH4Cl solution
  4. extractionextracted with hexane
  5. washthe extracts washed with water
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-81a27554c02e4f1b887385db98acc972
出典データセット
uspto-grants-1999_11
特許番号
US05977133

関連ノート

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