Sodium Thiosulfate → 5-Benzyl-2-(2,5-difluorophenyl)thiazole-4-carbaldehyde

HRID 404834Notes

Reaction equation

HRID 404834 reaction equation
[CH2:1]([C:8]1[S:12][C:11]([C:13]2[CH:18]=[C:17]([F:19])[CH:16]=[CH:15][C:14]=2[F:20])=[N:10][C:9]=1[CH2:21][OH:22])[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+].[O-]S([O-])(=S)=O.[Na+].[Na+]>ClCCl>[CH2:1]([C:8]1[S:12][C:11]([C:13]2[CH:18]=[C:17]([F:19])[CH:16]=[CH:15][C:14]=2[F:20])=[N:10][C:9]=1[CH:21]=[O:22])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 67450892(5-Benzyl-2-(2,5-difluorophenyl)thiazol-4-yl)methanol

Product 1

HCID 866938875-Benzyl-2-(2,5-difluorophenyl)thiazole-4-carbaldehydeYield 80.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (5-benzyl-2-(2,5-difluorophenyl)thiazol-4-yl)methanol (6.66 g, 20.99 mmol) in dichloromethane (70.0 mL) was added Dess-Martin periodinane (13.35 g, 31.5 mmol). The reaction mixture was stirred at room temperature for overnight. 200 mL of saturated NaHCO3 solution and saturated Na2S2O3 solution (8:1) was added for quenching the reaction. After stirred for 1 h, the reaction mixture was extracted by EtOAc. The organic layers was washed with water and brine, dried over anhydrous Na2SO4, filtered, and concentrated. The crude product was purified by column chromatography to yield 5-benzyl-2-(2,5-difluorophenyl)thiazole-4-carbaldehyde (5.3 g, 80%) as white solid. 1H NMR (CDCl3, 400 MHz): δ 10.3 (1H, s), 8.01 (1H, m), 7.36-7.17 (5H, m), 7.16-7.07 (2H, m), 4.64 (2H, s). LC/MS (uplc): MH+ 316.2, 1.21 min.

Workup

  1. customfor quenching
  2. customthe reaction
  3. stirringAfter stirred for 1 h
  4. extractionthe reaction mixture was extracted by EtOAc
  5. washThe organic layers was washed with water and brine
  6. dry with materialdried over anhydrous Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-d5fdff71d23a47519c6e7386ba8caa1b
Source dataset
uspto-grants-2014_06
Patent number
US08748626B2

Reaction notes

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