Triacetoxyperiodinane → 3-(4-Phenylbutoxy)propionaldehyde

HRID 1966621Notes

Reaction equation

HRID 1966621 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][O:11][CH2:12][CH2:13][CH2:14][OH:15])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][O:11][CH2:12][CH2:13][CH:14]=[O:15])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 672465283-(4-Phenylbutoxy)propan-1-ol

Product 1

HCID 866583073-(4-Phenylbutoxy)propionaldehydeYield 58.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of Intermediate 12 (1.0 g, 4.8 mmol) in CH2Cl2 (20 mL) was added Dess-Martin periodinane (2.4 g, 5.76 mmol) and the reaction was stirred 2 hours at room temperature. The solution was then diluted with CH2Cl2 (40 mL), washed with water (2×20 mL), saturated solution of sodium bicarbonate (2×20 mL), and water (20 mL), dried (Na2SO4), and concentrated. The residue was purified by column chromatography (methylene chloride/acetone, 20:1) to afford the title compound (580 mg, 58%) as oil.

Workup

  1. washwashed with water (2×20 mL), saturated solution of sodium bicarbonate (2×20 mL), and water (20 mL)
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated
  4. customThe residue was purified by column chromatography (methylene chloride/acetone, 20:1)

Sources & evidence

ORD record
ord-834ca94df74f41a7a8f4b3bae5d462c8
Source dataset
uspto-grants-2013_04
Patent number
US08420669B2

Reaction notes

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