Sodium hydride → 5-(Cyclobutoxymethyl)benzofuran

HRID 2075163ノート

反応式

HRID 2075163 の反応式
[CH:1]1([OH:5])[CH2:4][CH2:3][CH2:2]1.[H-].[Na+].Br[CH2:9][C:10]1[CH:11]=[CH:12][C:13]2[O:17][CH:16]=[CH:15][C:14]=2[CH:18]=1>CN(C=O)C.O>[CH:1]1([O:5][CH2:9][C:10]2[CH:11]=[CH:12][C:13]3[O:17][CH:16]=[CH:15][C:14]=3[CH:18]=2)[CH2:4][CH2:3][CH2:2]1

参加物

6

反応物 3

HCID 24758Sodium hydrideHCID 76218CyclobutanolHCID 221285225-(Bromomethyl)benzofuran

生成物 1

HCID 584153505-(Cyclobutoxymethyl)benzofuran

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
0 °C

実験手順

A mixture of cyclobutanol (1.0 mL, 14.0 mmol) and sodium hydride (0.5 g, 14.0 mmol) in DMF (20 mL) was stirred at 0° C. for 30 minutes. 5-(Bromomethyl)benzofuran (2.9 g, 14.0 mmol) was the added and resultant reaction mixture was slowly warmed to room temperature and left stirring over night. Reaction mixture was diluted to 100 mL with water. The solution was extracted with Et2O (20 mL×3); the combined extracts were washed with 1N NaOH solution, water and brine, dried, and concentrated under reduced pressure to yield the desired product after purification on silica (4/1 hexane/ethyl acetate). 1H NMR (400 MHz, CDCl3) δ 7.58 (d, 2H), 7.42 (d, 1H), 7.27 (d, 1H), 6.78 (s, 1H), 4.54 (s, 2H) 4.03 (m, 1H), 2.21 (m, 2H), 1.94 (m, 2H), 1.76 (m, 1H), 1.52 (m, 1H).

後処理

  1. additionadded
  2. customresultant reaction mixture
  3. temperaturewas slowly warmed to room temperature
  4. waitleft
  5. stirringstirring over night
  6. customReaction mixture
  7. extractionThe solution was extracted with Et2O (20 mL×3)
  8. washthe combined extracts were washed with 1N NaOH solution, water and brine
  9. customdried
  10. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-70d071907057470e94b8d4c591bb2261
出典データセット
uspto-grants-2011_04
特許番号
US07919519B2

反応ノート

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