Triphenylphosphine → Methyl 2-benzoyl-6-ethyl-3,5-dihydroxy-phenylacetate

HRID 499872Notes

Reaction equation

C([O:4][C:5]1[C:6]([C:22](=[O:29])[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[C:7]([CH2:17][C:18]([O:20][CH3:21])=[O:19])[C:8]([CH2:15][CH3:16])=[C:9]([O:11]CC=C)[CH:10]=1)C=C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(O)(=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:22]([C:6]1[C:5]([OH:4])=[CH:10][C:9]([OH:11])=[C:8]([CH2:15][CH3:16])[C:7]=1[CH2:17][C:18]([O:20][CH3:21])=[O:19])(=[O:29])[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

Conditions

Temperature: 80 °C

Procedure

Methyl 3,5-diallyloxy-2-benzoyl-6-ethylphenylacetate (0.29 g, 0.72 mmol) obtained in Example 5, Step 4 was dissolved in acetic acid (5.0 mL) in an atmosphere of argon. To the solution were added triphenylphosphine (74 mg, 0.28 mmol) and palladium (II) acetate (16 mg, 0.071 mmol), followed by stirring at 80° C. for 5 hours. To the reaction mixture were further added triphenylphosphine (0.15 g, 0.57 mmol) and palladium (II) acetate (32 mg, 0.14 mmol), followed by stirring at 100° C. for 13 hours. The reaction mixture was cooled to room temperature and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (ethyl acetate/hexane=1/9-3/1) to obtain Compound 5 (0.23 g, 60%).

Workup

stirringby stirring at 100° C. for 13 hours
temperatureThe reaction mixture was cooled to room temperature
concentrationconcentrated under reduced pressure
customThe resulting residue was purified by silica gel column chromatography (ethyl acetate/hexane=1/9-3/1)

Sources & evidence

ORD record: ord-d14d7e6323594c67bfe4768116e2c866
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07767693B2

Reaction notes

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