Tetrahydrofuran → 3-Methoxypropiophenone

HRID 1974500Notes

Reaction equation

HRID 1974500 reaction equation
CO[C:3]1[CH:4]=[C:5]([Br:9])[CH:6]=[CH:7][CH:8]=1.[Mg:10].[C:11]([O:15][C:16](=O)[CH2:17][CH3:18])(=[O:14])CC.[Cl-].[NH4+].[O:22]1[CH2:26][CH2:25][CH2:24][CH2:23]1>C(OCC)C>[CH3:11][O:15][C:16]1[CH:17]=[C:18]([Mg:10][Br:9])[CH:23]=[CH:24][CH:25]=1.[CH3:23][O:22][CH2:26][CH2:25][C:24]([C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1)=[O:14]

Participants

8

Reactant 5

HCID 8028TetrahydrofuranHCID 169713-BromoanisoleHCID 25517Ammonium ChlorideHCID 31263Propionic anhydrideHCID 5462224Magnesium

Product 2

HCID 109427883-MethoxypropiophenoneHCID 178490745HCID 178490745, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
-70 °C

Procedure

A solution of 3-methoxyphenylmagnesium bromide in tetrahydrofuran (500 ml) was prepared from 3-methoxybromobenzene (187 g) and magnesium turnings (24 g) and was added over 1.5 hours to a mixture of propionic anhydride (260 g) and diethyl ether (500 ml) which had been cooled to -70° C. A saturated aqueous solution of ammonium chloride (500 ml) was added and the mixture was allowed to warm to ambient temperature. The organic layer was separated and washed in turn with a dilute aqueous sodium hydroxide solution and with a saturated aqueous sodium chloride solution. The organic layer was dried (Na2SO4) and evaporated to give 3-methoxypropiophenone as a yellow oil (160 g).

Workup

  1. temperatureto warm to ambient temperature
  2. customThe organic layer was separated
  3. washwashed in turn with a dilute aqueous sodium hydroxide solution and with a saturated aqueous sodium chloride solution
  4. dry with materialThe organic layer was dried (Na2SO4)
  5. customevaporated

Sources & evidence

ORD record
ord-fc4ba2e664f747a3a484a3b7a88a4093
Source dataset
uspto-grants-1994_02
Patent number
US05283245

Reaction notes

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