Triphenylphosphine → Ethyl 3-(chloromethyl)-5-(dimethylamino)benzoate

HRID 2368874Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2368874
[CH3:1][N:2]([CH3:16])[C:3]1[CH:4]=[C:5]([CH:11]=[C:12]([CH2:14]O)[CH:13]=1)[C:6]([O:8][CH2:9][CH3:10])=[O:7].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C(=O)N([Cl:43])C(=O)C1>C(Cl)Cl>[Cl:43][CH2:14][C:12]1[CH:11]=[C:5]([CH:4]=[C:3]([N:2]([CH3:16])[CH3:1])[CH:13]=1)[C:6]([O:8][CH2:9][CH3:10])=[O:7]

Komponenten

5

Edukt 3

HCID 11776TriphenylphosphineHCID 31398ChlorosuccinimideHCID 68335184Ethyl 3-(dimethylamino)-5-(hydroxymethyl)benzoate

Produkt 1

HCID 68335175Ethyl 3-(chloromethyl)-5-(dimethylamino)benzoateAusbeute 96 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of Compound 2 (3.45 g, 15.452 mmol) and PPh3 (6.14 g, 23.17 mmol) in 70 mL of DCM was added NCS (3.19 g, 23.178 mmol) at 0° C. The reaction mixture was stirred for 1.5 hours. After removal of solvent under reduced pressure, the residue was dissolved in Et2O. The solution was washed with brine and dried with MgSO4. The solution was filtered and concentrated. The residue was subjected to chromatography over silica gel (Hexanes/EtOAc=9.5/0.5) to give Compound 3 (3.585 g, 96%). 1H-NMR (500 MHz, CDCl3) δ 7.38 (s, 1H), 7.35 (s, 1H), 6.89 (s, 1H), 4.57 (s, 2H), 4.37 (q, J=7.1 Hz, 2H), 3.00 (s, 6H), 1.39 (t, J=7.1 Hz, 3H); 13C-NMR (125 MHz, CDCl3) δ 166.73, 150.63, 138.35, 131.59, 117.31, 116.20, 113.22, 60.95, 46.40, 40.43, 14.31; ESI-MS: m/z (MH+): 242.0942 (calc'd), 242.0944 (found).

Aufarbeitung

  1. customAfter removal of solvent under reduced pressure
  2. dissolutionthe residue was dissolved in Et2O
  3. washThe solution was washed with brine
  4. dry with materialdried with MgSO4
  5. filtrationThe solution was filtered
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-64a0cd2b68f24191bab7483321b13776
Quelldatensatz
uspto-grants-2014_04
Patentnummer
US08703815B2

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