Dimethyl Sulfate → HCID 22452654, Verbindung

HRID 2185878Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2185878
[I:1][C:2]1[C:11]2[CH2:10][CH2:9][CH2:8][CH2:7][C:6]=2[CH:5]=[C:4]([C:12]([OH:14])=[O:13])[C:3]=1O.S([O:21][CH3:22])(OC)(=O)=O.[C:23]([O-])([O-])=O.[K+].[K+].C(N(CC)CC)C>CC(C)=O>[I:1][C:2]1[C:11]2[CH2:10][CH2:9][CH2:8][CH2:7][C:6]=2[CH:5]=[C:4]([C:12]([O:14][CH3:23])=[O:13])[C:3]=1[O:21][CH3:22]

Komponenten

6

Edukt 4

HCID 6497Dimethyl SulfateHCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 22452633HCID 22452633, Verbindung

Produkt 1

HCID 22452654HCID 22452654, VerbindungAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

To a stirred suspension of 4-iodo-3-hydroxy-5,6,7,8-tetrahydro-2-naphthalenecarboxylic acid (23.43 g, 73.65 mmol) in dry acetone (450 mL) was added dimethyl sulfate (17.42 mL, 184.13 mmol) and K2CO3 (25.45 g, 184.13 mmol). The mixture was stirred at reflux overnight, cooled and triethylamine (40 mL) was added. After 0.5 h the mixture was filtered through a pad of diatomaceous earth and the filtrate concentrated in vacuo. The residue was dissolved in ethyl acetate (50 mL) and washed successively with 1N HCl (2×50 mL), sat. aqueous sodium bicarbonate (2×50 mL) and brine (50 mL ), dried (Na2SO4), filtered and concentrated in vacuo to afford a brown oil (22.52 g, 90%). 1H NMR (CDCl3) δ 7.56 (s, 1H), 3.92 (s, 3H), 3.85 (s, 3H), 2.69 (m, 4H), 1.79 (m, 4H). MS m/z 347 (M+H).

Aufarbeitung

  1. temperatureat reflux overnight
  2. temperaturecooled
  3. filtrationAfter 0.5 h the mixture was filtered through a pad of diatomaceous earth
  4. concentrationthe filtrate concentrated in vacuo
  5. dissolutionThe residue was dissolved in ethyl acetate (50 mL)
  6. washwashed successively with 1N HCl (2×50 mL), sat. aqueous sodium bicarbonate (2×50 mL) and brine (50 mL )
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-e74ef2ac30314ac28e255248793da22e
Quelldatensatz
uspto-grants-2002_06
Patentnummer
US06403601B1

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