Water → HCID 86661715, Verbindung

HRID 77349

Reaktionsgleichung

Reaktionsgleichung von HRID 77349
[PH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7](/[C:10](/[CH3:26])=[CH:11]/[C:12]([O:14][C:15]2[C:20]([Cl:21])=[C:19]([Cl:22])[C:18]([Cl:23])=[C:17]([Cl:24])[C:16]=2[Cl:25])=[O:13])=[CH:6][CH:5]=1)=[O:2].[OH-:27].[Na+].[C:29]([O:35][CH2:36]I)(=[O:34])[C:30]([CH3:33])([CH3:32])[CH3:31].[OH2:38]>[N+]([O-])([O-])=O.[Ag+]>[CH3:31][C:30]([CH3:33])([CH3:32])[C:29](=[O:34])[O:35][CH2:36][O:2][P:1]([O:38][CH2:36][O:35][C:29](=[O:34])[C:30]([CH3:33])([CH3:32])[CH3:31])([O:3][C:4]1[CH:5]=[CH:6][C:7](/[C:10](/[CH3:26])=[CH:11]/[C:12]([O:14][C:15]2[C:16]([Cl:25])=[C:17]([Cl:24])[C:18]([Cl:23])=[C:19]([Cl:22])[C:20]=2[Cl:21])=[O:13])=[CH:8][CH:9]=1)=[O:27]

Komponenten

6

Edukt 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 104401Iodomethyl pivalateHCID 178454638HCID 178454638, Verbindung

Produkt 1

HCID 86661715HCID 86661715, VerbindungAusbeute 69 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 24470Silver NitrateKatalysator

Versuchsvorschrift

(13b1 R1=pivaloyloxymethyl) To a stirred suspension of 12b1 (1.0 g, 1.97 mmol) in 10 mL of water, NaOH (158 mg, 3.94 mmol) in 2 mL of water was added. The mixture became clear (pH-9). A 5 mL aqueous solution of AgNO3 (807 mg, 4.75 mmol), was added. After 3 h of stirring at room temperature, the gray precipitate was collected by filtration, dried over P2O5, and pulverized in a mortar and pestle. The powder was suspended in dry toluene (15 mL) and pivaloyloxymethyl iodide (1.4 g, 5.7 mmol) was added and the mixture was stirred for 48 h at room temperature. After filtration the solvent was removed in vacuo and the crude product was purified by silica gel column chromatography eluting with 30% EtOAc-hexanes to give colorless sticky liquid (1.0 g, 69%). 1H NMR (CDCl3, 500 MHz) δ 1.22 (s, 18H), 2.64 (s, 3H), 5.73-5.8 (m, 4H), 6.43 (s, 1H), 7.31 (d, J=8.0 Hz, 2H), 7.58 (d, J=8.0 Hz, 2H). 13C NMR (CDCl3, 125 MHz) δ 18.5, 26.8, 38.7, 83.1, 113.8, 120.4, 127.9, 128.2, 131.3, 132.0, 138.6, 144.3, 151.3, 160.4, 161.9, 176.6. HRMS (M+H) calc, 733.0097; found, 733.0122

Aufarbeitung

  1. additionwas added
  2. filtrationthe gray precipitate was collected by filtration
  3. dry with materialdried over P2O5
  4. stirringthe mixture was stirred for 48 h at room temperature
  5. filtrationAfter filtration the solvent
  6. customwas removed in vacuo
  7. customthe crude product was purified by silica gel column chromatography
  8. washeluting with 30% EtOAc-hexanes

Quellen und Nachweise

ORD-Eintrag
ord-b0033aa02cf04c27b89c30d03c53cddf
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08841257B2

Verknüpfte Notizen

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