Ethyl Acetate → HCID 86680497, compound

HRID 1777478Notes

Reaction equation

HRID 1777478 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:9][C:10]([CH:13]([C:15]3[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=3)[OH:14])=[CH:11][N:12]=2)=[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+].C(OCC)(=O)C>C(Cl)Cl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[S:9][C:10]([C:13]([C:15]3[CH:16]=[CH:17][N:18]=[CH:19][CH:20]=3)=[O:14])=[CH:11][N:12]=2)=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 71544406HCID 71544406, compound

Product 1

HCID 86680497HCID 86680497, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of (2-(4-fluorophenyl)thiazol-5-yl)(pyridin-4-yl)methanol (0.55 g, 1.92 mol) in DCM (20 mL) was added Dess-Martin periodinane (1.6 g, 3.84 mol) at room temperature. The resulting solution was stirred for 1 h. To the reaction mixture was added NaHCO3 solution (20 mL) and ethyl acetate (50 mL). The organic layer was extracted with ethyl acetate (2×20 mL), washed with brine solution (2×20 mL), dried over anhydrous sodium sulfate and the solvent removed via distillation under reduced pressure. The crude was purified through silica gel (100-200 mesh) column chromatography using 10% methanol in DCM) to obtain (2-(4-fluorophenyl)thiazol-5-yl)(pyridin-4-yl)methanone as off-white solid (0.4 g, 67% yield). 1H NMR (400 MHz, DMSO-d6): δ 8.86 (d, 2H), 8.51 (s, 1H), 8.19 (dd, 2H), 7.82 (d, 2H), 7.45 (t, 2H); LC-MS m/z calculated for [M+H]+ 285.04 found 284.98.

Workup

  1. extractionThe organic layer was extracted with ethyl acetate (2×20 mL)
  2. washwashed with brine solution (2×20 mL)
  3. dry with materialdried over anhydrous sodium sulfate
  4. customthe solvent removed via distillation under reduced pressure
  5. customThe crude was purified through silica gel (100-200 mesh) column chromatography

Sources & evidence

ORD record
ord-d2607c07bfb043a88de427a5c3584db5
Source dataset
uspto-grants-2016_02
Patent number
US09266873B2

Reaction notes

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