4-(Cyclopropylmethyl)benzaldehyde → HCID 19010837, compound

HRID 1741831Notes

Reaction equation

HRID 1741831 reaction equation
[CH2:1]([Mg]Br)[CH:2]=[CH2:3].[CH:6]1([CH2:9][C:10]2[CH:17]=[CH:16][C:13]([CH:14]=[O:15])=[CH:12][CH:11]=2)[CH2:8][CH2:7]1>C(OCC)C>[CH:6]1([CH2:9][C:10]2[CH:11]=[CH:12][C:13]([CH:14]([OH:15])[CH2:3][CH:2]=[CH2:1])=[CH:16][CH:17]=2)[CH2:8][CH2:7]1

Participants

4

Reactant 2

HCID 190108254-(Cyclopropylmethyl)benzaldehydeHCID 178455850HCID 178455850, compound

Product 1

HCID 19010837HCID 19010837, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a solution of allylmagnesium bromide (1.0M in diethyl ether, 3 ml) in diethyl ether (5 ml) was added dropwise 4-(cyclopropylmethyl)benzaldehyde (240 mg) in diethyl ether (2 ml) at 0° C. After 15 minutes, the reaction mixture was quenched by aqueous ammonium chloride and the resulting mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over magnesium sulfate and concentrated. The residue was chromatographed on silica gel column eluting with a mixture of hexane and ethyl acetate (85:15) to give 1-[4-(cyclopropylmethyl)phenyl]-3-buten-1-ol (229 mg) as an oil.

Workup

  1. customthe reaction mixture was quenched by aqueous ammonium chloride
  2. extractionthe resulting mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with water
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. customThe residue was chromatographed on silica gel column
  7. washeluting with a mixture of hexane and ethyl acetate (85:15)

Sources & evidence

ORD record
ord-44ce09d171884f7296faad4eddb0ccbd
Source dataset
uspto-grants-1994_08
Patent number
US05334716

Reaction notes

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