Water → 1-[4-(Benzyloxy)-3-(3-methoxypropyl)phenyl]ethanone

HRID 922457Notes

Reaction equation

HRID 922457 reaction equation
C(O[C:5]1[C:10]2C=CO[C:9]=2[CH:8]=[C:7]([C:14]([O:16][CH2:17][CH3:18])=O)[CH:6]=1)(=O)C.[C:19](=[O:22])([O-])[O-].[K+].[K+].[CH3:25][C:26]1[CH:31]=[CH:30][C:29](S(OCCCOC)(=O)=O)=[CH:28][CH:27]=1.[OH2:41].[C:42](#N)[CH3:43]>>[CH2:14]([O:16][C:17]1[CH:18]=[CH:25][C:26]([C:31](=[O:41])[CH3:30])=[CH:27][C:28]=1[CH2:29][CH2:42][CH2:43][O:22][CH3:19])[C:7]1[CH:6]=[CH:5][CH:10]=[CH:9][CH:8]=1

Participants

6

Reactant 5

HCID 962WaterHCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 135229883-Methoxypropyl 4-methylbenzenesulfonateHCID 675451626-Benzofurancarboxylic acid, 4-(acetyloxy)-, ethyl ester

Product 1

HCID 899254421-[4-(Benzyloxy)-3-(3-methoxypropyl)phenyl]ethanone

Procedure

To a solution of the compound obtained in the above (1) (11.0 g) in acetonitrile (113 mL) were added potassium carbonate (9.37 g) and 3-methoxypropyl 4-methylbenzene sulfonate (13.2 g), and the mixture was heated to reflux for 20 hours. The reaction solution was cooled to room temperature, and then thereto was added water, and the mixture was extracted with ethyl acetate. The organic layer was dried over magnesium sulfate, and then concentrated under reduced pressure. The resulting residue was triturated with diisopropyl ether to give 1-[4-(benzyloxy)-3-(3-methoxypropyl)phenyl]ethanone [REx(26-2)] (8.75 g) as a colorless powder.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 20 hours
  3. extractionthe mixture was extracted with ethyl acetate
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue was triturated with diisopropyl ether

Sources & evidence

ORD record
ord-c099472c67e54e0793101c235007953b
Source dataset
uspto-grants-2016_03
Patent number
US09278944B2

Reaction notes

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