Hydrochloric Acid → methyl (E) 2-[3-(4-acetoxy-1,3-dihydro-6-methoxy-7-methyl-3-oxoisobenzofuran-5-yl)-prop-1-en-1-yl]-3-methylbenzoate

HRID 2396649Notes

Reaction equation

HRID 2396649 reaction equation
[C:1]([O:4][C:5]1[C:13]([CH2:14][CH:15]=[CH2:16])=[C:12]([O:17][CH3:18])[C:11]([CH3:19])=[C:10]2[C:6]=1[C:7](=[O:20])[O:8][CH2:9]2)(=[O:3])[CH3:2].Br[C:22]1[C:31]([CH3:32])=[CH:30][CH:29]=[CH:28][C:23]=1[C:24]([O:26][CH3:27])=[O:25].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.Cl>C(=O)([O-])[O-].[Ag+2].C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CN(C)C=O>[C:1]([O:4][C:5]1[C:13]([CH2:14]/[CH:15]=[CH:16]/[C:22]2[C:31]([CH3:32])=[CH:30][CH:29]=[CH:28][C:23]=2[C:24]([O:26][CH3:27])=[O:25])=[C:12]([O:17][CH3:18])[C:11]([CH3:19])=[C:10]2[C:6]=1[C:7](=[O:20])[O:8][CH2:9]2)(=[O:3])[CH3:2]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 11776TriphenylphosphineHCID 10823279Methyl 2-Bromo-3-methylbenzoateHCID 190463174-Acetoxy-5-allyl-1,3-dihydro-6-methoxy-7-methyl-3-oxoisobenzofuran

Product 1

HCID 86749277methyl (E) 2-[3-(4-acetoxy-1,3-dihydro-6-methoxy-7-methyl-3-oxoisobenzofuran-5-yl)-prop-1-en-1-yl]-3-methylbenzoate

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 178418647HCID 178418647, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

4-Acetoxy-5-allyl-1,3-dihydro-6-methoxy-7-methyl-3-oxoisobenzofuran (0.6 g), methyl 2-bromo-3-methylbenzoate (0.92 g), silver carbonate (1.3 g), palladium acetate (0.1 g), triphenylphosphine (0.14 g) and dimethylformamide (70 ml) were heated with stirring at 100° C. for 6 hours, then stirred at ambient temperature for 18 hours. The mixture was poured into ice water and the pH adjusted to 3 by addition of 2N hydrochloric acid. The mixture was extracted with ethyl acetate, and the extract was dried and evaporated. The residue was chromatographed on silica gel, eluting with 7:3 hexane:ethyl acetate, to give methyl (E) 2-[3-(4-acetoxy-1,3-dihydro-6-methoxy-7-methyl-3-oxoisobenzofuran-5-yl)-prop-1-en-1-yl]-3-methylbenzoate, mp 104°-111° C. (ethyl acetate/hexane).

Workup

  1. stirringstirred at ambient temperature for 18 hours
  2. extractionThe mixture was extracted with ethyl acetate
  3. customthe extract was dried
  4. customevaporated
  5. customThe residue was chromatographed on silica gel
  6. washeluting with 7:3 hexane

Sources & evidence

ORD record
ord-4cfec3b83ff04aa28a0217528d969d46
Source dataset
uspto-grants-1996_02
Patent number
US05493030

Reaction notes

Loading…