Triethylamine → (2-Methoxy-6-methylbenzyl)phthalimide

HRID 1157847

Reaktionsgleichung

Reaktionsgleichung von HRID 1157847
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][CH:8]=[C:7]([CH3:11])[C:4]=1[CH2:5]O.C(N(CC)CC)C.CS(Cl)(=O)=O.[C:24]1(=[O:34])[NH:28][C:27](=[O:29])[C:26]2=[CH:30][CH:31]=[CH:32][CH:33]=[C:25]12.[K]>C(Cl)Cl.CN(C=O)C.CCOC(C)=O.[Cl-].[Na+].O.O>[CH3:1][O:2][C:3]1[CH:10]=[CH:9][CH:8]=[C:7]([CH3:11])[C:4]=1[CH2:5][C:33]1[CH:32]=[CH:31][CH:30]=[C:26]2[C:27]([NH:28][C:24](=[O:34])[C:25]=12)=[O:29]

Komponenten

10

Edukt 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 13208697(2-Methoxy-6-methylphenyl)methanolHCID 24194345Phthalimide potassium salt

Produkt 1

HCID 21985073(2-Methoxy-6-methylbenzyl)phthalimideAusbeute 66,4 %

Reagenzien, Katalysatoren, Lösungsmittel 5

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittelHCID 57417360Sodium chloride; waterLösungsmittel

Versuchsvorschrift

To a solution of 2-methoxy-6-methylbenzyl alcohol (0.96 g, 6.32 mmol) in CH2Cl2 (35 mL) was added triethylamine (2.00 mL, 14.35 mmol) followed by methanesulfonyl chloride (0.90 mL, 11.63 mmol) and the resultant solution was heated at 40° C. for 45 minutes then cooled to room temperature. The mixture was diluted with CH2Cl2 (35 mL), washed with brine (3×15 mL), dried (Na2SO4), and concentrated to provide a pale yellow solid. The solid (1.12 g) was dissolved in DMF (35 mL), treated with potassium phthalimide (2.62 g, 14.15 mmol), and heated at 80° C. overnight. The mixture was cooled to room temperature and diluted with EtOAc (70 mL), brine (35 mL), and water (20 mL). The phases were separated and the organic phase was washed with 1.0 N NaOH (6×10 mL) and brine (2×20 mL). The organic phase was dried (MgSO4) and concentrated to provide an pale yellow solid. The solid was rinsed with hexanes (3×10 mL) and provided 1.18 g (66%) of (2-methoxy-6-methylbenzyl)phthalimide as a white solid. 1H NMR (CDCl3) δ 2.53 (s, 3H), 3.75 (s, 3H), 4.89 (s, 2H), 6.70 (d, 1H, J=8.4 Hz), 6.80 (d, 1H, J=7.5 Hz), 7.15 (dd, 1H, J=7.5, 8.4 Hz), 7.66-7.68 (m, 2H), 7.76-7.80 (m, 2H); 13C NMR (CDCl3) δ 20.27, 34.95, 55.90, 108.61, 122.38, 123.17, 123.41, 128.97, 132.60, 134.07, 139.55, 158.70, 168.36.

Aufarbeitung

  1. washwashed with brine (3×15 mL)
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated
  4. customto provide a pale yellow solid
  5. temperatureheated at 80° C. overnight
  6. temperatureThe mixture was cooled to room temperature
  7. customThe phases were separated
  8. washthe organic phase was washed with 1.0 N NaOH (6×10 mL) and brine (2×20 mL)
  9. dry with materialThe organic phase was dried (MgSO4)
  10. concentrationconcentrated
  11. customto provide an pale yellow solid
  12. washThe solid was rinsed with hexanes (3×10 mL)

Quellen und Nachweise

ORD-Eintrag
ord-1e7199fda11c4d378ef4cc3b63d39371
Quelldatensatz
uspto-grants-2010_10
Patentnummer
US07807694B2

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