HCID 19885941, compound → HCID 19885887, compound

HRID 654933Notes

Reaction equation

HRID 654933 reaction equation
[C:1]1([CH2:7][CH2:8]/[CH:9]=[CH:10]/[CH2:11][CH2:12][CH2:13][CH2:14][C:15](OCC)=[O:16])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].C([Al+]CC(C)C)C(C)C>C(Cl)Cl>[C:1]1([CH2:7][CH2:8]/[CH:9]=[CH:10]/[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][OH:16])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 19885941HCID 19885941, compoundHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 19885887HCID 19885887, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of (E)-ethyl 9-phenylnon-6-enoate (1.45 g, 5.53 mmol) in methylene chloride (35 ml) under argon at 0° was added diisobutylaluminum hydride (15.0 ml of a 1.0M solution). This mixture was warmed to room temperature and quenched with 10% aqueous hydrochloric acid. The organic portion was washed with saturated sodium bicarbonate solution, water, saturated sodium chloride solution, dried over magnesium sulfate, filtered and concentrated to give a colorless oil. Purification by flash chromatography (silica, 20% ethyl acetate/hexane) gave the desired alcohol.

Workup

  1. customquenched with 10% aqueous hydrochloric acid
  2. washThe organic portion was washed with saturated sodium bicarbonate solution, water, saturated sodium chloride solution
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give a colorless oil
  7. customPurification by flash chromatography (silica, 20% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-75c619b3f0a64d2392f03bfd11f45606
Source dataset
uspto-grants-1992_07
Patent number
US05134128

Reaction notes

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