Ethyl Acetate → 3-(3-Cyclopentoxy-4-methoxyphenyl)propenyl alcohol

HRID 1073751Notes

Reaction equation

HRID 1073751 reaction equation
[CH:1]1([O:6][C:7]2[CH:8]=[C:9](/[CH:15]=[CH:16]/[C:17](OC)=[O:18])[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].C([Al+]CC(C)C)C(C)C.[Cl-].[NH4+].C(OCC)(=O)C>C(Cl)Cl.C1(C)C=CC=CC=1.CCCCCC>[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([CH2:15][CH:16]=[CH:17][OH:18])[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

8

Reactant 4

HCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 5702848methyl 3-(3-cyclopentoxy-4-methoxyphenyl)-E-propenoateHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 700560933-(3-Cyclopentoxy-4-methoxyphenyl)propenyl alcohol

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 6344DichloromethaneSolventHCID 8058HexaneSolvent

Procedure

To a stirred solution of 0.50 g (1.81 mmol) of methyl 3-(3-cyclopentoxy-4-methoxyphenyl)-E-propenoate in 70 mL of dry methylene chloride under a nitrogen atmosphere was added dropwise 3.0 mL (3.0 mmol) of a 1.0M solution of diisobutylaluminum hydride in toluene over a 10 minute period at room temperature. The mixture was stirred for 30 minutes at the end of which time the solution was slowly poured over a stirring solution of 30 mL of saturated ammonium chloride. The resulting solution was stirred for 30 minutes during which time a gelatinous solid formed. Absorption of the solid on excess Celite 545 followed by filtration over a pad of Celite 545 and elution with three, 30 mL portions of chloroform provided a yellow suspension. Separation of the layers followed by washing the organic fraction with 30 mL of saturated sodium chloride, drying over magnesium sulfate and concentration gave a crude yellow product. Liquid chromatography over 100 g of silica gel eluting with 30% ethyl acetate in hexane provided the desired, analytically pure product after drying in vacuo.

Workup

  1. stirringThe resulting solution was stirred for 30 minutes during which time a gelatinous solid
  2. customformed
  3. customAbsorption of the solid on excess Celite 545
  4. filtrationfollowed by filtration over a pad of Celite 545 and elution with three, 30 mL portions of chloroform
  5. customprovided a yellow suspension
  6. customSeparation of the layers
  7. washby washing the organic fraction with 30 mL of saturated sodium chloride
  8. dry with materialdrying over magnesium sulfate and concentration
  9. customgave a crude yellow product
  10. customanalytically pure product after drying in vacuo

Sources & evidence

ORD record
ord-49b6f7e3b2c94123a92c26f809ead3bb
Source dataset
uspto-grants-1990_11
Patent number
US04971959

Reaction notes

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