Water → Cyclopentyl(3,5-dimethoxyphenyl)methanone

HRID 417054Notes

Reaction equation

HRID 417054 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([O:11][CH3:12])[CH:10]=1)[C:6]#N.[CH:13]1([Mg]Cl)[CH2:17][CH2:16][CH2:15][CH2:14]1.O.S(=O)(=O)(O)[OH:22]>C1COCC1.C(OCC)C>[CH:13]1([C:6]([C:5]2[CH:4]=[C:3]([O:2][CH3:1])[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=2)=[O:22])[CH2:17][CH2:16][CH2:15][CH2:14]1

Participants

7

Reactant 4

HCID 962WaterHCID 1118Sulfuric AcidHCID 294821-(Cyanomethyl)-3,5-dimethoxybenzeneHCID 178478989HCID 178478989, compound

Product 1

HCID 11543194Cyclopentyl(3,5-dimethoxyphenyl)methanoneYield 82%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3,5-dimethoxybenzonitrile (5.0 g) in anhydrous THF (60 mL) were added a solution of cyclopentylmagnesium chloride (20 mL of 2 M solution in diethyl ether) and cuprous bromide (88 mg). The resulting reaction mixture was refluxed for 1 h. Then water (10 mL) and 10% sulfuric acid (20 mL) were added and the resulting mixture was stirred at room temperature overnight. Then the reaction mixture was diluted with diethyl ether and 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 5.9 of the title compound (82% yield). HRMS calcd for C14H18O3 [M+H]+ 253.1329, observed 253.1328.

Workup

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

Sources & evidence

ORD record
ord-834c853154724f7ab769e0844b4cdc2f
Source dataset
uspto-grants-2012_01
Patent number
US08088936B2

Reaction notes

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