Ethylene Glycol → 5-(2-Ethyl-1,3-dioxolan-2-yl)benzofuran

HRID 626250Notes

Reaction equation

HRID 626250 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10](=[O:13])[CH2:11][CH3:12])=[CH:9][C:4]=2[CH:3]=[CH:2]1.[CH2:14](O)[CH2:15][OH:16].CC1C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH2:11]([C:10]1([C:8]2[CH:7]=[CH:6][C:5]3[O:1][CH:2]=[CH:3][C:4]=3[CH:9]=2)[O:16][CH2:15][CH2:14][O:13]1)[CH3:12]

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 6101p-Toluenesulfonic acidHCID 673362701-(Benzofuran-5-yl)propan-1-one

Product 1

HCID 896574105-(2-Ethyl-1,3-dioxolan-2-yl)benzofuranYield 87.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 1-(benzofuran-5-yl)propan-1-one (650 mg, 1.0 eq), ethane-1,2-diol (3.5 g, 15.0 eq) and 4-methylbenzenesulfonic acid (65 mg, 0.1 eq) in 20 mL toluene was refluxed for 72 h, cooled, quenched with sat. NaHCO3 (aq) and extracted with EtOAc. The extract was washed with brine, dried, concentrated, and purified by column chromatography to give the desired product (710 mg, 87%). 1H NMR (400 MHz, CDCl3) δ 7.69 (d, J=2.0 Hz, 1H), 7.62 (d, J=2.4 Hz, 1H), 7.45 (d, J=8.4 Hz, 1H), 7.39 (dd, J=8.4 Hz, 1.6 Hz, 1H), 6.76 (dd, J=2.4 Hz, 0.4 Hz, 1H), 4.02-4.05 (m, 2H), 3.78-3.81 (m, 2H), 1.96 (q, J=7.2 Hz, 2H), 0.89 (t, J=7.2 Hz, 3H).

Workup

  1. temperaturecooled
  2. customquenched with sat. NaHCO3 (aq)
  3. extractionextracted with EtOAc
  4. washThe extract was washed with brine
  5. customdried
  6. concentrationconcentrated
  7. custompurified by column chromatography

Sources & evidence

ORD record
ord-4d9099c6d5594c5bba9a234ee5dbe31f
Source dataset
uspto-grants-2016_04
Patent number
US09309211B2

Reaction notes

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