Water → 2-(4-Methyl-1-oxo-1,3-dihydro-2-benzofuran-5-yl)propanal

HRID 2173174Notes

Reaction equation

HRID 2173174 reaction equation
[OH:1][CH2:2][CH:3]([C:5]1[CH:14]=[CH:13][C:8]2[C:9](=[O:12])[O:10][CH2:11][C:7]=2[C:6]=1[CH3:15])[CH3:4].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C1=CC=CC=2)=O.[O-]S([O-])(=S)=O.[Na+].[Na+].O>C(Cl)Cl>[CH3:15][C:6]1[C:7]2[CH2:11][O:10][C:9](=[O:12])[C:8]=2[CH:13]=[CH:14][C:5]=1[CH:3]([CH3:4])[CH:2]=[O:1]

Participants

6

Reactant 4

HCID 962WaterHCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 666438615-(2-hydroxy-1-methylethyl)-4-methyl-2-benzofuran-1(3H)-one

Product 1

HCID 595687262-(4-Methyl-1-oxo-1,3-dihydro-2-benzofuran-5-yl)propanal

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

5-(2-Hydroxy-1-methylethyl)-4-methyl-2-benzofuran-1(3H)-one (161 mg, 0.781 mmol, 1.0 eq) was dissolved in DCM (6 mL). To above solution was added Dess-MartinPeriodinane (397 mg, 0.937 mmol, 1.2 eq). The reaction was stirred at rt for 2 hr. To the reaction was added DCM (10 mL), Na2S2O3 (6 mL) and H2O (6 mL). The mixture was stirred at r.t. for 30 minutes and formed two layers. The bottom layer was separated and washed with aqueous NaHCO3, brine and water, dried over Na2SO4, filtered, and concentrated to dryness. The crude product was used to next step without purification. 1H NMR (500 MHz, CDCl3, δ in ppm): 9.70 (1H, s, CHO), 7.79 (1H, d, J=7.8 Hz), 7.28 (1H, d, J=7.8 Hz), 5.28 (2H, s), 3.27 (1H, m), 2.32 (3H, s), 1.50 (3H, d, J=7.2 Hz).

Workup

  1. stirringThe mixture was stirred at r.t. for 30 minutes
  2. customformed two layers
  3. customThe bottom layer was separated
  4. washwashed with aqueous NaHCO3, brine and water
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated to dryness
  8. customThe crude product was used to next step without purification

Sources & evidence

ORD record
ord-a8f1d19ace3e43849e5f7d92fb372eb1
Source dataset
uspto-grants-2015_06
Patent number
US09056859B2

Reaction notes

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