Sodium hydride → 5-(Cyclobutoxymethyl)benzofuran

HRID 2075163노트

반응식

HRID 2075163 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

HCID 584153505-(Cyclobutoxymethyl)benzofuran

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

반응 조건

온도
0 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-70d071907057470e94b8d4c591bb2261
출처 데이터셋
uspto-grants-2011_04
특허 번호
US07919519B2

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