Methyl iodide → HCID 58934897、化合物

HRID 855157ノート

反応式

HRID 855157 の反応式
[F:1][C:2]1[CH:3]=[C:4]([CH:12]=[CH:13][CH:14]=1)[O:5][CH:6]1[CH2:11][CH2:10][CH2:9][CH2:8][O:7]1.[Li][CH2:16]CCC.CI>C1COCC1>[F:1][C:2]1[C:3]([CH3:16])=[C:4]([CH:12]=[CH:13][CH:14]=1)[O:5][CH:6]1[CH2:11][CH2:10][CH2:9][CH2:8][O:7]1

参加物

5

反応物 3

HCID 6328Methyl iodideHCID 157823112-(3-fluorophenoxy)tetrahydro-2H-pyranHCID 178418339Butyllithium

生成物 1

HCID 58934897HCID 58934897、化合物収率 90.1%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

To a chilled solution (−78° C.) of 9.33 g (47.55 mmol) of 2-(3-fluorophenoxy)-tetrahydro-2H-pyran in 150 mL of THF was added 38 mL (95.1 mmols) of n-BuLi (2.5 M soln in hexanes). The reaction mixture was stirred at −78° C. for 45 minutes and slowly added 11.9 mL (190.2 mmol) of methyl iodide via syringe. The reaction was allowed to warm to room temperature and was stirred overnight. Quenched reaction with satd ammonium chloride and transferred to a round bottom flask. Removed volatiles in vacuo and partitioned mixture between EtOAc and water. Separated layers and washed organics with water (×2) and brine. Dried over Na2SO4, filtered, and concd to afford a 9.01 g (90%) of a yellow oil: 1H NMR (CDCl3/400 MHz) 1.46-2.09 (m, 6H), 2.21 (d, 3H, J=2.0 Hz), 3.60-3.65 (m, 1H), 3.86-3.92 (m, 1H), 5.44 (t, 1H, J=3.2 Hz), 6.70 (t, 1H, J=8.8 Hz), 6.90 (d, 1H, J=8.4 Hz), 7.08 (dd, 1H, J=8.0, 15.2 Hz); HRMS (EI+) m/z calcd for (C12H15FO2) 210.1056, found 210.1070.

後処理

  1. temperatureto warm to room temperature
  2. stirringwas stirred overnight
  3. customQuenched
  4. customreaction with satd ammonium chloride
  5. customtransferred to a round bottom flask
  6. customRemoved volatiles in vacuo and partitioned mixture between EtOAc and water
  7. washSeparated layers and washed organics with water (×2) and brine
  8. dry with materialDried over Na2SO4
  9. filtrationfiltered

出典と根拠

ORDレコード
ord-0ceb9fef0726404d805ac0dead4c287a
出典データセット
uspto-grants-2007_08
特許番号
US07259266B2

反応ノート

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