3-Cyclopentyloxy-4-methoxybenzaldehyde → 1-(3-Cyclopentyloxy-4-methoxyphenyl)ethanol

HRID 893391Notes

Reaction equation

HRID 893391 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.[CH3:17][Li]>O1CCCC1>[CH3:17][CH:10]([OH:11])[C:9]1[CH:12]=[CH:13][C:14]([O:15][CH3:16])=[C:7]([O:6][CH:1]2[CH2:2][CH2:3][CH2:4][CH2:5]2)[CH:8]=1

Participants

4

Reactant 2

HCID 27358933-Cyclopentyloxy-4-methoxybenzaldehydeHCID 178418348HCID 178418348, compound

Product 1

HCID 219240271-(3-Cyclopentyloxy-4-methoxyphenyl)ethanolYield 99%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a magnetically-stirred solution of 3-cyclopentyloxy-4-methoxybenzaldehyde (59.0 mmol, 13.0 g) in dry tetrahydrofuran (500 mL) at -78° C. is added methyllithium (100 mmol, 90.0 mL; 1.4M solution in ethyl ether) dropwise over 30 minutes. The resulting solution is stirred at -78° C. for 30 minutes and quenched at -78° C. by the rapid addition of aqueous saturated NH4Cl (140 mL). After warming to room temperature, water is added to dissolve the solids and the tetrahydrofuran was removed in vacuo. The residue is partitioned between water (500 mL) and ethyl acetate (500 mL), the aqueous phase extracted with ethyl acetate (500 mL) and the combined organic layers are washed with water (500 mL). The organics are dried (Na2SO4) and concentrated in vacuo to afford the title compound as a light yellow oil (58.3 mmol, 13.7 g; 99%). This material is of sufficient purity by TLC and NMR to be used as such in the subsequent transformation.

Workup

  1. customquenched at -78° C. by the rapid addition of aqueous saturated NH4Cl (140 mL)
  2. temperatureAfter warming to room temperature
  3. additionwater is added
  4. dissolutionto dissolve the solids
  5. customthe tetrahydrofuran was removed in vacuo
  6. customThe residue is partitioned between water (500 mL) and ethyl acetate (500 mL)
  7. extractionthe aqueous phase extracted with ethyl acetate (500 mL)
  8. washthe combined organic layers are washed with water (500 mL)
  9. dry with materialThe organics are dried (Na2SO4)
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d0a927614e794091aefc097b364cc271
Source dataset
uspto-grants-1992_06
Patent number
US05124455

Reaction notes

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