Sodium Iodide → Methyl 4-((di-tert-butoxyphosphoryloxy)methyl)benzoate

HRID 595040

Reaktionsgleichung

Reaktionsgleichung von HRID 595040
Br[CH2:2][C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][CH:4]=1.[P:13]([O-:25])([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14].[K+].[I-].[Na+]>CN(C=O)C.CCOCC>[C:21]([O:20][P:13]([O:25][CH2:2][C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][CH:4]=1)([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])([CH3:24])([CH3:23])[CH3:22]

Komponenten

6

Edukt 3

HCID 5238Sodium IodideHCID 256687Methyl 4-(bromomethyl)benzoateHCID 23674467Potassium di-tert-butyl phosphate

Produkt 1

HCID 90087888Methyl 4-((di-tert-butoxyphosphoryloxy)methyl)benzoate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Methyl 4-(bromomethyl)benzoate (1200 mg, 5.24 mmol), potassium di-tert-butyl phosphate (1431 mg, 5.76 mmol) and sodium iodide (785 mg, 5.24 mmol) were combined in DMF (3.00 mL) under nitrogen. The reaction mixture was stirred at room temperature for 24 h. The reaction mixture was diluted with ether, washed with 10% LiCl solution and brine, then dried (MgSO4), filtered and concentrated in vacuo. The residue was purified by silica gel chromatography (hexane/EtOAc) to provide Preparation 55A (571 mg, 1.593 mmol, 30%): 1H NMR (400 MHz, CDCl3) δ 8.03 (d, J=8.4 Hz, 2H), 7.53-7.37 (m, 2H), 5.05 (d, J=7.5 Hz, 2H), 3.92 (s, 3H), 1.48 (d, J=0.4 Hz, 18H).

Aufarbeitung

  1. washwashed with 10% LiCl solution and brine
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by silica gel chromatography (hexane/EtOAc)
  6. customto provide

Quellen und Nachweise

ORD-Eintrag
ord-ddb14697f5774d0e8ba27545822bb64b
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09242941B2

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