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

HRID 922450
Notes
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Reaction equation

HRID 922450 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 5

HCID 962WaterHCID 11430Potassium CarbonateHCID 312751,4-DioxaneHCID 574072TrimethylboroxineHCID 675451626-Benzofurancarboxylic acid, 4-(acetyloxy)-, ethyl ester

Product 1

HCID 683105641-[3-(3-Methoxypropoxy)-5-methylphenyl]ethanone

Reagents, catalysts & solvents

1
HCID 44119782Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)Catalyst

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

  1. temperaturethe mixture was heated
  2. temperatureAfter cooling to room temperature
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with saturated saline
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes