Sulfuric Acid → 1-[3-Benzo[1,3]dioxol-5-yl-5-(4-methoxy-benzyloxy)-phenyl]-2-methyl-propan-1-one

HRID 417047Notes

Reaction equation

HRID 417047 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3[CH:11]=[C:12]([CH:15]=[C:16]([O:18][CH2:19][C:20]4[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=4)[CH:17]=3)[C:13]#N)=[CH:9][C:4]=2[O:3][CH2:2]1.[CH:28]([Mg]Cl)([CH3:30])[CH3:29].S(=O)(=O)(O)[OH:34]>C1COCC1.C(OCC)C>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3[CH:11]=[C:12]([C:13](=[O:34])[CH:28]([CH3:30])[CH3:29])[CH:15]=[C:16]([O:18][CH2:19][C:20]4[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=4)[CH:17]=3)=[CH:9][C:4]=2[O:3][CH2:2]1

Participants

6

Reactant 3

HCID 1118Sulfuric AcidHCID 594968393-Benzo[1,3]dioxol-5-yl-5-(4-methoxy-benzyloxy)-benzonitrileHCID 178418918HCID 178418918, compound

Product 1

HCID 594968191-[3-Benzo[1,3]dioxol-5-yl-5-(4-methoxy-benzyloxy)-phenyl]-2-methyl-propan-1-oneYield 64%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-benzo[1,3]dioxol-5-yl-5-(4-methoxy-benzyloxy)-benzonitrile (500 mg) in anhydrous THF (10 mL) were added a solution of isopropylmagnesium chloride (2.1 mL of 2 M solution in diethyl ether) and catalytic amount of cuprous bromide (4 mg). The resulting reaction mixture was refluxed for 2 h. After it was cooled down, 10% sulfuric acid (5 mL) was added and stirring was continued for 30 min at room temperature. Then the reaction mixture was diluted with diethyl ether, washed with water and brine. The organic extract was dried over anhydrous sodium sulfate, concentrated and purified on a silica gel column using ethyl acetate and hexanes to yield 358 mg of the title compound (64% yield). HRMS calcd for C25H24O5 [M+H]+ 405.1697, observed 405.1698.

Workup

  1. customThe resulting reaction mixture
  2. temperaturewas refluxed for 2 h
  3. temperatureAfter it was cooled down
  4. washwashed with water and brine
  5. extractionThe organic extract
  6. dry with materialwas dried over anhydrous sodium sulfate
  7. concentrationconcentrated
  8. custompurified on a silica gel column

Sources & evidence

ORD record
ord-5adc976157e041c1b8c8cb03e3034de1
Source dataset
uspto-grants-2012_01
Patent number
US08088936B2

Reaction notes

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