Tetrahydrofuran → 1-[4-Methoxy-3-(4-methoxybutyl)phenyl]ethanone

HRID 922454Notes

Reaction equation

HRID 922454 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[C:4]([CH2:10][CH2:11][CH2:12][CH2:13][O:14][CH3:15])[CH:3]=1.[Cl-].[Li+].[F-].[K+].[O:20]1CC[CH2:22][CH2:21]1>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:9][O:8][C:5]1[CH:6]=[CH:7][C:2]([C:21](=[O:20])[CH3:22])=[CH:3][C:4]=1[CH2:10][CH2:11][CH2:12][CH2:13][O:14][CH3:15]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 433294Lithium ChlorideHCID 522689Potassium FluorideHCID 214586274-Bromo-1-methoxy-2-(4-methoxybutyl)benzene

Product 1

HCID 867078661-[4-Methoxy-3-(4-methoxybutyl)phenyl]ethanone

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Conditions

Temperature
80 °C

Procedure

To a solution of 4-bromo-1-methoxy-2-(4-methoxybutyl)benzene (523 mg) in tetrahydrofuran (10 mL) were added lithium chloride (326 mg), tetrakis(triphenylphosphine)palladium (0) (381 mg) and tri-n-butyltin-1-ethoxyvinyl 91.11 mL), and the mixture was heated to stir at 80° C. for 20 hours. The reaction solution was cooled to room temperature, and then thereto was added aqueous potassium fluoride solution, and the mixture was stirred for 30 minutes. The mixture was extracted with diethyl ether, and then thereto was added 10% hydrochloric acid, and the mixture was stirred for 1 hour. The organic layer was separated, dried over magnesium sulfate, and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=9/1→1/1) to give 1-[4-methoxy-3-(4-methoxybutyl)phenyl]ethanone [REx(24-1)] (195 mg) as a yellow oil.

Workup

  1. temperaturewas heated
  2. temperatureThe reaction solution was cooled to room temperature
  3. stirringthe mixture was stirred for 30 minutes
  4. extractionThe mixture was extracted with diethyl ether
  5. additionwas added 10% hydrochloric acid
  6. stirringthe mixture was stirred for 1 hour
  7. customThe organic layer was separated
  8. dry with materialdried over magnesium sulfate
  9. concentrationconcentrated under reduced pressure
  10. customThe resulting residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=9/1→1/1)

Sources & evidence

ORD record
ord-ec3db68129f646a68435292c7338880d
Source dataset
uspto-grants-2016_03
Patent number
US09278944B2

Reaction notes

Loading…