Hydrochloric Acid → 1-(3-Cyclopentyloxy-4-methoxyphenyl)-3-methylbutan-1-ol

HRID 893394Notes

Reaction equation

HRID 893394 reaction equation
[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([CH:12]=[CH:13][C:14]=2[O:15][CH3:16])[CH:10]=[O:11])[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:17]([Mg]Cl)[CH:18]([CH3:20])[CH3:19].Cl>C(OCC)C>[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([CH:10]([OH:11])[CH2:17][CH:18]([CH3:20])[CH3:19])[CH:12]=[CH:13][C:14]=2[O:15][CH3:16])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 27358933-Cyclopentyloxy-4-methoxybenzaldehydeHCID 178418368HCID 178418368, compound

Product 1

HCID 198924961-(3-Cyclopentyloxy-4-methoxyphenyl)-3-methylbutan-1-olYield 86%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a magnetically-stirred solution of 3-cyclopentyloxy-4-methoxybenzaldehyde (25.0 mmol, 5.50 g) of Example 1A, in anhydrous ethyl ether (250 mL) at 0° C. is added isobutylmagnesium chloride (30 mmol, 15 mL; 2.0M solution in ethyl ether) dropwise over 20 minutes. The reaction mixture is allowed to stir while slowly warming to room temperature over 1 hour and is then poured into 1N HCl (250 mL) and partitioned with ethyl ether (200 mL). The aqueous phase is extracted with ethyl ether (200 mL) and the combined organics are washed with aqueous saturated NaHCO3 (200 mL), aqueous saturated NaCl (200 mL), and dried (MgSO4). Concentration in vacuo affords a yellow oil which is purified by flash chromatography (SiO2 : 1) methylene chloride, 2) 2% ethyl acetate/methylene chloride, 3) 5% ethyl acetate/methylene chloride) to give the title compound as a white solid (21.5 mmol, 5.98 g; 86 %).

Workup

  1. custompartitioned with ethyl ether (200 mL)
  2. extractionThe aqueous phase is extracted with ethyl ether (200 mL)
  3. washthe combined organics are washed with aqueous saturated NaHCO3 (200 mL), aqueous saturated NaCl (200 mL)
  4. dry with materialdried (MgSO4)
  5. concentrationConcentration in vacuo
  6. customaffords a yellow oil which
  7. customis purified by flash chromatography (SiO2 : 1) methylene chloride, 2) 2% ethyl acetate/methylene chloride, 3) 5% ethyl acetate/methylene chloride)

Sources & evidence

ORD record
ord-c7c63e00bec34551838130989a1351e9
Source dataset
uspto-grants-1992_06
Patent number
US05124455

Reaction notes

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