Water → 1-[3-(3-Methoxypropoxy)-5-methylphenyl]ethanone

HRID 922450Notes

Reaction equation

C(O[C:5]1[C:10]2[CH:11]=[CH:12][O:13][C:9]=2[CH:8]=[C:7]([C:14](OCC)=O)[CH:6]=1)(=O)C.[C:19](=[O:22])([O-])[O-].[K+].[K+].[CH3:25]B1OB(C)OB(C)O1.O.[O:35]1[CH2:40]COC[CH2:36]1>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH3:36][O:35][CH2:40][CH2:11][CH2:12][O:13][C:9]1[CH:10]=[C:5]([C:19](=[O:22])[CH3:25])[CH:6]=[C:7]([CH3:14])[CH:8]=1

Participants

Conditions

Temperature: 110 °C

Procedure

To a solution of the compound obtained in the (1) (8.22 g) in 1,4-dioxane 9100 mL) were added potassium carbonate (8.6 g), trimethylboroxine (3.5 mL) and 1,1′-bis(diphenylphosphino)ferrocene dichloropalladium (II) (1.51 g), and the mixture was heated to stir at 110° C. for 2 hours. After cooling to room temperature, thereto was added water, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated saline, dried over sodium sulfate, and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent: n-hexane→n-hexane/ethyl acetate=5/1) to give 1-[3-(3-methoxypropoxy)-5-methylphenyl]ethanone [REx(21-2)] (4.15 g) as a brown oil.

Workup

temperaturethe mixture was heated
temperatureAfter cooling to room temperature
extractionthe mixture was extracted with ethyl acetate
washThe organic layer was washed with saturated saline
dry with materialdried over sodium sulfate
concentrationconcentrated under reduced pressure
customThe resulting residue was purified by silica gel column chromatography (eluent: n-hexane→n-hexane/ethyl acetate=5/1)

Sources & evidence

ORD record: ord-094b9d722302499786841d5949b24691
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09278944B2

Reaction notes

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