Sodium hydride → 5-(Cyclobutoxymethyl)benzofuran

HRID 2075163Notes

Reaction equation

HRID 2075163 reaction equation
[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

Participants

6

Reactant 3

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

Product 1

HCID 584153505-(Cyclobutoxymethyl)benzofuran

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-70d071907057470e94b8d4c591bb2261
Source dataset
uspto-grants-2011_04
Patent number
US07919519B2

Reaction notes

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