1,8-Diazabicyclo(5.4.0)undec-7-ene → 5-ethenyl-6-methyl-2-benzofuran-1(3H)-one

HRID 1466094Notes

Reaction equation

HRID 1466094 reaction equation
CS(O[CH2:6][CH2:7][C:8]1[C:17]([CH3:18])=[CH:16][C:11]2[C:12](=[O:15])[O:13][CH2:14][C:10]=2[CH:9]=1)(=O)=O.C1CCN2C(=NCCC2)CC1>C(Cl)Cl>[CH:7]([C:8]1[C:17]([CH3:18])=[CH:16][C:11]2[C:12](=[O:15])[O:13][CH2:14][C:10]=2[CH:9]=1)=[CH2:6]

Participants

4

Reactant 2

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 866472962-(6-Methyl-1-oxo-1,3-dihydro-2-benzofuran-5-yl)ethyl methanesulfonate

Product 1

HCID 666438115-ethenyl-6-methyl-2-benzofuran-1(3H)-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a mixture of 2-(6-methyl-1-oxo-1,3-dihydro-2-benzofuran-5-yl)ethyl methanesulfonate (2.00 g, 7.41 mmol) and TEA (5 mL) in DCM (50 mL) was added DBU (5 mL) slowly at 0° C. The mixture was stirred at r.t. overnight, and then was diluted with 50 mL of DCM, washed with 2 N HCl three times and brine. The organic layer was dried and concentrated to dryness. The residue was purified by prep-TLC to give 5-ethenyl-6-methyl-2-benzofuran-1(3H)-one.

Workup

  1. washwashed with 2 N HCl three times and brine
  2. customThe organic layer was dried
  3. concentrationconcentrated to dryness
  4. customThe residue was purified by prep-TLC

Sources & evidence

ORD record
ord-5be24cd36ca9429ea3a69f495da11fe7
Source dataset
uspto-grants-2015_04
Patent number
US08999990B2

Reaction notes

Loading…