Ethanol → HCID 57780771, compound

HRID 1668432Notes

Reaction equation

HRID 1668432 reaction equation
CCO.Cl[C:5]1[O:9][C:8]([C:10]2[C:14]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[C:13]([CH3:21])[O:12][N:11]=2)=[CH:7][CH:6]=1.[K+].[Br-]>O=[Pt]=O.CCCCCC>[O:9]1[CH:5]=[CH:6][CH:7]=[C:8]1[C:10]1[C:14]([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)=[C:13]([CH3:21])[O:12][N:11]=1

Participants

6

Reactant 3

HCID 702EthanolHCID 253877Potassium BromideHCID 10355223HCID 10355223, compound

Product 1

HCID 57780771HCID 57780771, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 8058HexaneSolvent

Procedure

A solution of EtOH (2 ml) containing 3-(5-chlorofuran-2-yl)-4-phenyl-5-methylisoxazole (97 mg, 0.374 mmoles), PtO2 (5 mg) is kept in an atmosphere of H2 (1 atm) at ambient temperature, stirring for 7 h. The catalyst is then filtered on celite and the solvent is evaporated at reduced pressure. The residue is crystallised from hexane. A white powder is obtained with 89% yield and a m.p. 93-96° C. (hexane). FT-IR (KBr): 3149, 3122, 3059, 2962, 2925, 2853, 1633, 1605, 1511, 1496, 1448, 1438, 1417, 1239, 1225, 1176, 1070, 1020, 976, 923, 891, 782, 714, 700 cm−1. 1H NMR (400 MHz, CDCl3, δ): 7.47-7.41 (m, 4H, aromatic protons); 7.31-7.28 (m, 2H, aromatic protons); 6.37-6.35 (dd, 1H, J=3.3 Hz, J=1.8 Hz, furyl proton); 6.34-6.33 (d, 1H, J=3.3 Hz, furyl proton); 2.39 (s, 3H). 13C NMR (100 MHz, CDCl3, δ): 166.6, 153.1, 144.0, 143.6, 130.0, 129.8, 128.7, 128.1, 114.9, 111.5, 111.1, 11.2. GC-MS (70 eV) m/z (rel.int.): 225 (M+, 40), 184 (14), 183 (100), 154 (17), 127 (13), 102 (12), 43 (11). Anal. Calc. for C14H11NO2: C, 74.65; H, 4.92; N, 6.22; O, 14.21. Found: C, 74.48; H, 4.94; N, 6.19.

Workup

  1. customis kept in an atmosphere of H2 (1 atm) at ambient temperature
  2. filtrationThe catalyst is then filtered on celite
  3. customthe solvent is evaporated at reduced pressure
  4. customThe residue is crystallised from hexane
  5. customA white powder is obtained with 89% yield

Sources & evidence

ORD record
ord-67cb5451270a4ca188abd28cf9bb6fb4
Source dataset
uspto-grants-2011_08
Patent number
US07989450B2

Reaction notes

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