Sodium Thiosulfate → 2-methyl-2-(tetrahydro-2H-pyran-2-yloxy)propanal

HRID 2386269Notes

Reaction equation

HRID 2386269 reaction equation
[CH3:1][C:2]([O:6][CH:7]1[CH2:12][CH2:11][CH2:10][CH2:9][O:8]1)([CH3:5])[CH2:3][OH:4].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.C([O-])(O)=O.[Na+].[O-]S([O-])(=S)=O.[Na+].[Na+]>ClCCl>[CH3:5][C:2]([O:6][CH:7]1[CH2:12][CH2:11][CH2:10][CH2:9][O:8]1)([CH3:1])[CH:3]=[O:4]

Participants

6

Reactant 4

HCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 242096552-Methyl-2-[(tetrahydro-2H-pyran-2-yl)oxy]-1-propanol

Product 1

HCID 859020802-methyl-2-(tetrahydro-2H-pyran-2-yloxy)propanalYield 83.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 2-methyl-2-(tetrahydro-2H-pyran-2-yloxy)propan-1-ol (1.16 g, 6.68 mmol) in dichloromethane (20 ml) at 0° C. was added portionwise Dess-Martin periodinane (3.26 g, 7.68 mmol), and the reaction mixture was stirred at the same temperature for 20 minutes, followed by addition of saturated aqueous NaHCO3 and Na2S2O3. The resulting mixture was stirred for 3 hours and the reaction mixture was extracted with Et2O. The combined organic phases were dried and concentrated in vacuo to give 2-methyl-2-(tetrahydro-2H-pyran-2-yloxy)propanal (958 mg, 5.56 mmol, 83% yield) as a colorless oil which was used in the next step without further purification. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.18 (s, 3H) 1.23 (s, 3 H) 1.33-1.85 (m, 6H) 3.32-3.44 (m, 1H) 3.73-3.89 (m, 1H) 4.61-4.70 (m, 1H) 9.44 (s, 1 H).

Workup

  1. stirringThe resulting mixture was stirred for 3 hours
  2. extractionthe reaction mixture was extracted with Et2O
  3. customThe combined organic phases were dried
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-94586ecd8e3146ff94e5811c53b58cc4
Source dataset
uspto-grants-2012_09
Patent number
US08268819B2

Reaction notes

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