Ethyl Acetate → HCID 9903701, compound

HRID 1830978Notes

Reaction equation

HRID 1830978 reaction equation
[C:1]1([C:7]2[CH:8]=[CH:9][C:10]3[N:16](C(OCC(Cl)(Cl)Cl)=O)[CH2:15][CH:14]4[CH2:25][CH2:26][CH2:27][N:13]4[C:12](=[O:28])[C:11]=3[CH:29]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([O-])(=O)C.[NH4+].C(OCC)(=O)C>C1COCC1>[C:1]1([C:7]2[CH:8]=[CH:9][C:10]3[N:16]=[CH:15][C@@H:14]4[CH2:25][CH2:26][CH2:27][N:13]4[C:12](=[O:28])[C:11]=3[CH:29]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 517165Ammonium AcetateHCID 86588597HCID 86588597, compound

Product 1

HCID 9903701HCID 9903701, compoundYield 98.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Cd/Pb (0.47 g) couple was added portion wise to a vigorously stirred solution of 135 (0.33 g, 0.7 mmol) in THF (5 mL) and of aq. ammonium acetate (1M, 5 mL). The suspension was allowed to stir at room temperature for 2 hours, then poured into ethyl acetate (200 mL), dried with MgSO4 and filtered. The filtrate was evaporated and the residue purified by flash column chromatography (ethyl acetate) to afford the title compound as colourless oil (0.19 g, 98%): 1H NMR (270 MHz, CDCl3) δ2.0-2.12 (m, 2H); 2.29-2.37 (m, 2H); 3.53-3.63 (m, 1H); 3.76-3.92 (m, 2H); 7.36-7.79 (m, 8H); 8.28 (d, J=2.2 Hz, 1H). 13C NMR (67.8 MHz, CDCl3) δ24.4; 29.8; 46.9; 53.8; 126.9; 127.3; 127.7; 128.0; 128.2; 128.8; 128.9; 129.1; 130.1; 130.5; 139.5; 145.0; 164.5; 165.1. IR (Nujol): cm−1 3000-2800, 1620, 1455, 1377, 1239, 1239, 1014, 990, 761,728, 697. HRMS Calculated for C18H16N2O: 276.1261. Found: 276.1262. [α]25D=+131.4° (c=0.19, CHCl3).

Workup

  1. dry with materialdried with MgSO4
  2. filtrationfiltered
  3. customThe filtrate was evaporated
  4. customthe residue purified by flash column chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-e50af1d5dc294e419bdd13aaf51e4bd6
Source dataset
uspto-grants-2006_06
Patent number
US07067511B2

Reaction notes

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