3-Cyclopentyloxy-4-methoxybenzaldehyde → alpha-(3-Cyclopentyloxy-4-methoxyphenyl)benzylalcohol

HRID 232789Notes

Reaction equation

HRID 232789 reaction equation
[C:1]1([Li])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:8]1([O:13][C:14]2[CH:15]=[C:16]([CH:19]=[CH:20][C:21]=2[O:22][CH3:23])[CH:17]=[O:18])[CH2:12][CH2:11][CH2:10][CH2:9]1>O1CCCC1>[C:1]1([CH:17]([OH:18])[C:16]2[CH:19]=[CH:20][C:21]([O:22][CH3:23])=[C:14]([O:13][CH:8]3[CH2:9][CH2:10][CH2:11][CH2:12]3)[CH:15]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 27358933-Cyclopentyloxy-4-methoxybenzaldehydeHCID 178506676HCID 178506676, compound

Product 1

HCID 10565992alpha-(3-Cyclopentyloxy-4-methoxyphenyl)benzylalcoholYield 91.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

Phenyllithium (1.8M solution in cyclohexane/diethyl ether, 25.5 milliliters, 46 mmol) was added dropwise over 15 minutes to a stirred solution of 3-cyclopentyloxy-4-methoxybenz-aldehyde (6 grams, 27 mmol) in dry tetrahydrofuran (20 milliliters) at -78° C. The resulting solution was stirred at -78° C. for 30 minutes and quenched at -78° C. by the rapid addition of aqueous saturated NH4Cl (70 milliliters). After warming to room temperature, water was added to dissolve the solids and volatiles were removed in vacuo. The residue was partitioned between water (250 milliliters) and ethyl acetate (250 milliliters), the aqueous phase was extracted with ethyl acetate (3×250 milliliters) and the combined organic layers washed with water (200 milliliters). The organics were dried over Na2SO4 and concentrated in vacuo to give a light yellow oil. The oil was purified by flash chromatography (SiO2 :hexane/ethyl acetate (4:1)) to afford the title compound as a pale yellow oil (7.4 grams) .

Workup

  1. customquenched at -78° C. by the rapid addition of aqueous saturated NH4Cl (70 milliliters)
  2. temperatureAfter warming to room temperature
  3. additionwater was added
  4. dissolutionto dissolve the solids and volatiles
  5. customwere removed in vacuo
  6. customThe residue was partitioned between water (250 milliliters) and ethyl acetate (250 milliliters)
  7. extractionthe aqueous phase was extracted with ethyl acetate (3×250 milliliters)
  8. washthe combined organic layers washed with water (200 milliliters)
  9. dry with materialThe organics were dried over Na2SO4
  10. concentrationconcentrated in vacuo
  11. customto give a light yellow oil
  12. customThe oil was purified by flash chromatography (SiO2 :hexane/ethyl acetate (4:1))

Sources & evidence

ORD record
ord-e30c01d3fb0e4e36bcfc34d3b9316709
Source dataset
uspto-grants-1997_01
Patent number
US05591776

Reaction notes

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