Diethylene Glycol → 2-Ethyl-6-methoxy-1-benzofuran

HRID 2112287Notes

Reaction equation

HRID 2112287 reaction equation
NN.C(O)COCCO.[C:10]([C:13]1[O:14][C:15]2[CH:21]=[C:20]([O:22][CH3:23])[CH:19]=[CH:18][C:16]=2[CH:17]=1)(=O)[CH3:11].[OH-].[K+]>O>[CH2:10]([C:13]1[O:14][C:15]2[CH:21]=[C:20]([O:22][CH3:23])[CH:19]=[CH:18][C:16]=2[CH:17]=1)[CH3:11]

Participants

6

Reactant 4

HCID 8117Diethylene GlycolHCID 9321HydrazineHCID 14797Potassium HydroxideHCID 405411-(6-Methoxy-2-benzofuranyl)ethanone

Product 1

HCID 221436002-Ethyl-6-methoxy-1-benzofuranYield 97.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
190 °C

Procedure

Hydrazine (4.11 g, 69.4 mmol, up to 55%, Aldrich) was added to diethylene glycol solution of 2-acetyl-6-methoxybenzofuran (3.30 g, 17.3 mmol) . The mixture was heated to a temperature of 190° C. and stirred for 10 min. After cooled down to room temperature, potassium hydroxide (2.92 g, 52.1 mmol) was added, stirred in a range of 120° C. to 130° C. for 6 hours. Following this, the reaction solution was poured into water, extracted by dichloromethane, dried over MgSO4, and was concentrated under reduced pressure. Oil residue was purified by HPLC (silica gel, CHCl3) and target product (2.98 g, 16.9 mmol, 97%) was obtained.

Workup

  1. temperatureAfter cooled down to room temperature
  2. stirringstirred in a range of 120° C. to 130° C. for 6 hours
  3. extractionextracted by dichloromethane
  4. dry with materialdried over MgSO4
  5. concentrationwas concentrated under reduced pressure
  6. customOil residue was purified by HPLC (silica gel, CHCl3)

Sources & evidence

ORD record
ord-df20f798722c4a1888bb3cc535f87208
Source dataset
uspto-grants-2009_04
Patent number
US07521570B2

Reaction notes

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