Sodium Thiosulfate → 2-(3-(Benzyloxy)phenyl)acetaldehyde

HRID 2389341Notes

Reaction equation

HRID 2389341 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH2:15][CH2:16][OH:17])[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.C([O-])(O)=O.[Na+].S([O-])([O-])(=O)=S.[Na+].[Na+]>C(Cl)Cl.C(OCC)C>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH2:15][CH:16]=[O:17])[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 204025442-(3-(Benzyloxy)phenyl)ethanol

Product 1

HCID 115721302-(3-(Benzyloxy)phenyl)acetaldehyde

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-[3-(benzyloxy)phenyl]ethanol (700 mg) in DCM (10 mL) was added Dess-Martin periodinane (1.43 g) at 0° C. The reaction mixture was stirred for 5 hours at ambient temperature. The mixture was diluted with diethylether (25 mL), and the resulting suspension was added to saturated NaHCO3 aqueous solution (15 mL) and saturated sodium thiosulfate aqueous solution (15 mL). After the mixture was stirred for 10 minutes, the organic layer was washed with brine. The organic layer was dried over anhydrous MgSO4, filtered and evaporated in vacuo. The residue was purified by silica gel column chromatography (n-hexane:EtOAc=90:10-70:30) to give a [3-(benzyloxy)phenyl]acetaldehyde.

Workup

  1. stirringAfter the mixture was stirred for 10 minutes
  2. washthe organic layer was washed with brine
  3. dry with materialThe organic layer was dried over anhydrous MgSO4
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customThe residue was purified by silica gel column chromatography (n-hexane:EtOAc=90:10-70:30)

Sources & evidence

ORD record
ord-dc7b7b0adc2c408db58de69c620ea448
Source dataset
uspto-grants-2012_09
Patent number
US08273745B2

Reaction notes

Loading…