Bis(2-bromoethyl) ether → 4-(3-Methoxyphenyl)oxane-4-carbonitrile

HRID 1868668

反応式

HRID 1868668 の反応式
[H-].[Na+].[CH3:3][O:4][C:5]1[CH:6]=[C:7]([CH2:11][C:12]#[N:13])[CH:8]=[CH:9][CH:10]=1.Br[CH2:15][CH2:16][O:17][CH2:18][CH2:19]Br>CN1C(=O)CCC1>[CH3:3][O:4][C:5]1[CH:6]=[C:7]([C:11]2([C:12]#[N:13])[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)[CH:8]=[CH:9][CH:10]=1

参加物

5

反応物 3

HCID 21521Bis(2-bromoethyl) etherHCID 24758Sodium hydrideHCID 88310(3-Methoxyphenyl)acetonitrile

生成物 1

HCID 187863664-(3-Methoxyphenyl)oxane-4-carbonitrile収率 93.5%

試薬・触媒・溶媒 1

HCID 13387N-methyl-2-pyrrolidone溶媒

反応条件

温度
0 °C

実験手順

A mixture of NaH (3.2 g, 79 mmol) in 50 mL NMP stirred at 0° C., was treated dropwise with a mixture of 2-(3-methoxyphenyl)acetonitrile (3.9 g, 26 mmol) and 1-bromo-2-(2-bromoethoxy)ethane (6.1 g, 26 mmol) in 20 mL. The mixture was allowed to warm to room temperature and stirred for 15 hours, M+1=218. The mixture was then carefully quenched with 100 mL H2O and the pH was adjusted to 5. The mixture was extracted with ether (3×100 mL). The combined organic layers were washed with H2O (3×50 mL) and brine (20 mL). The organic layer was dried over anhydrous Na2SO4, concentrated in vacuo, and purified by column chromatography eluting with 10-20% EtOAc/hexane to give 5.28 g of the crude product 5.28 g as a pale yellow oil. MS (m/z)=218 (M+H)+.

後処理

  1. temperatureto warm to room temperature
  2. stirringstirred for 15 hours
  3. customThe mixture was then carefully quenched with 100 mL H2O
  4. extractionThe mixture was extracted with ether (3×100 mL)
  5. washThe combined organic layers were washed with H2O (3×50 mL) and brine (20 mL)
  6. dry with materialThe organic layer was dried over anhydrous Na2SO4
  7. concentrationconcentrated in vacuo
  8. custompurified by column chromatography
  9. washeluting with 10-20% EtOAc/hexane

出典と根拠

ORDレコード
ord-b3c61d16b4bf41a7a9fc7033fef635f9
出典データセット
uspto-grants-2009_12
特許番号
US07635715B2

関連ノート

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