Triacetoxyperiodinane → 1-(4-(5-Benzylbenzofuran-2-yl)-3-fluorophenyl)ethanone

HRID 2075274Notes

Reaction equation

HRID 2075274 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[CH2:23]([C:30]1[CH:31]=[CH:32][C:33]2[O:37][C:36]([C:38]3[CH:43]=[CH:42][C:41]([CH:44]([OH:46])[CH3:45])=[CH:40][C:39]=3[F:47])=[CH:35][C:34]=2[CH:48]=1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH2:23]([C:30]1[CH:31]=[CH:32][C:33]2[O:37][C:36]([C:38]3[CH:43]=[CH:42][C:41]([C:44](=[O:46])[CH3:45])=[CH:40][C:39]=3[F:47])=[CH:35][C:34]=2[CH:48]=1)[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

5

Reactant 3

HCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 584152741-(4-(5-Benzylbenzofuran-2-yl)-3-fluorophenyl)ethanol

Product 1

HCID 584153111-(4-(5-Benzylbenzofuran-2-yl)-3-fluorophenyl)ethanone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dess-Martin reagent (0.411 g, 0.970 mmol) was added to a solution of 1-(4-(5-benzylbenzofuran-2-yl)-3-fluorophenyl)ethanol (0.280 g, 0.808 mmol) in DCM (25 mL) and stirred at room temperature for 1 h. The mixture was treated with saturated aqueous NaHCO3, stirred for 5 min, and extracted with DCM. The combined organic layers were dried over MgSO4 and evaporated. Purification by flash chromatography using EtOAc/hexanes gave 1-(4-(5-benzylbenzofuran-2-yl)-3-fluorophenyl)ethanone. 1H NMR (300 MHz, CDCl3) δ ppm 8.11 (t, J=7.7 Hz, 1H), 7.68-7.88 (m, 2H), 7.41-7.48 (m, 2H), 7.12-7.35 (m, 7H), 4.09 (s, 2H), 2.63 (s, 3H). MS (ESI) m/z: Calculated; 344.4 Observed: 345.0 (M++1).

Workup

  1. stirringstirred for 5 min
  2. extractionextracted with DCM
  3. dry with materialThe combined organic layers were dried over MgSO4
  4. customevaporated
  5. customPurification by flash chromatography

Sources & evidence

ORD record
ord-8ee883e9615e4d4c8ec9f1db2e439f33
Source dataset
uspto-grants-2011_04
Patent number
US07919519B2

Reaction notes

Loading…