Triacetoxyperiodinane → 6-Butylbenzofuran-2-carbaldehyde

HRID 629151Notes

Reaction equation

HRID 629151 reaction equation
[CH2:1]([C:5]1[CH:15]=[CH:14][C:8]2[CH:9]=[C:10]([CH2:12][OH:13])[O:11][C:7]=2[CH:6]=1)[CH2:2][CH2:3][CH3:4].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.C(=O)(O)[O-].[Na+]>ClCCl>[CH2:1]([C:5]1[CH:15]=[CH:14][C:8]2[CH:9]=[C:10]([CH:12]=[O:13])[O:11][C:7]=2[CH:6]=1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 118228971(6-Butylbenzofuran-2-yl)methanol

Product 1

HCID 1182289706-Butylbenzofuran-2-carbaldehydeYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (6-butylbenzofuran-2-yl)methanol (85 mg, 0.42 mmol) in 1.5 mL dichloromethane at room temperature was added Dess-Martin periodinane (247 mg, 0.58 mmol). The resulting suspension was stirred vigorously for 2 h at room temperature, poured into 20 mL saturated sodium bicarbonate and extracted with dichloromethane (3×15 mL). The combined dichloromethane extracts were dried over magnesium sulfate, filtered and concentrated. The crude mixture was subjected to chromatography on silica gel (5% ethyl acetate in hexanes) to give 6-butylbenzofuran-2-carbaldehyde (81 mg, 96%) as an oil. Used without further characterization.

Workup

  1. extractionextracted with dichloromethane (3×15 mL)
  2. dry with materialThe combined dichloromethane extracts were dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-4e657b18fa964044a536ec9fb1074abc
Source dataset
uspto-grants-2016_04
Patent number
US09315495B2

Reaction notes

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