Isopropenyl acetate → Methyl 5-(propan-2-one-yl)benzofuran-2-carboxylic acid

HRID 1779454Notes

Reaction equation

HRID 1779454 reaction equation
[CH3:1][C:2]1[C:6]2[CH:7]=[C:8](Br)[CH:9]=[CH:10][C:5]=2[O:4][C:3]=1[C:12]([OH:14])=[O:13].C[O-].C([Sn+](CCCC)CCCC)CCC.C([O:33][C:34]([CH3:36])=[CH2:35])(=O)C.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:1][C:2]1[C:6]2[CH:7]=[C:8]([CH2:35][C:34](=[O:33])[CH3:36])[CH:9]=[CH:10][C:5]=2[O:4][C:3]=1[C:12]([OH:14])=[O:13]

Participants

7

Reactant 4

HCID 7916Isopropenyl acetateHCID 80271Tri-o-tolylphosphineHCID 23888285-Bromo-3-methyl-1-benzofuran-2-carboxylic acidHCID 11964040Methoxytri-n-butylstannane

Product 1

HCID 19079807Methyl 5-(propan-2-one-yl)benzofuran-2-carboxylic acid

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolvent

Procedure

A solution of methyl 5-bromobenzofuran-2-carboxylic acid (2.4 g, 9.3 mmol), tributyltin methoxide (4.0 mL, 14 mmol), isopropenyl acetate (1.4 mL, 14 mmol), palladium (II) acetate (0.1 g, 0.5 mmol) and tri-o-tolylphosphine (0.3 g, 1 mmol) in toluene (6 mL) were heated at 95° C. for 2 hours. The reaction solution was concentrated in vacuo and subjected to flash chromatography on silica gel (25% ethyl acetate:hexanes) to afford the title compound as a colorless solid, (1.8 g; m.p. 77°-79° C., Analytical calculated for C13H12O4 : C, 67.25; H, 5.21. Found: C, 67.12; H, 4.95).

Workup

  1. concentrationThe reaction solution was concentrated in vacuo

Sources & evidence

ORD record
ord-e21e4509d75a484b8533cc714b0d1cba
Source dataset
uspto-grants-1997_05
Patent number
US05627200

Reaction notes

Loading…