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Methane, dichloromethoxy- → methyl (R)-7-(4-fluorophenyl)-7-(3-formyl-6-hydroxy-2,4,5-trimethylphenyl)heptanoate

HRID 1707814
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1707814
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([C:18]2[C:23]([CH3:24])=[CH:22][C:21]([CH3:25])=[C:20]([CH3:26])[C:19]=2[OH:27])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([O:16][CH3:17])=[O:15])=[CH:4][CH:3]=1.[CH3:28][O:29]C(Cl)Cl>ClCCl.[Ti](Cl)(Cl)(Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([C:18]2[C:19]([OH:27])=[C:20]([CH3:26])[C:21]([CH3:25])=[C:22]([CH:28]=[O:29])[C:23]=2[CH3:24])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([O:16][CH3:17])=[O:15])=[CH:4][CH:3]=1
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Komponenten

5

Edukt 2

HCID 21004Methane, dichloromethoxy-HCID 10714337methyl (R)-7-(4-fluorophenyl)-7-(2-hydroxy-3,4,6-trimethylphenyl)heptanoate

Produkt 1

HCID 10644683methyl (R)-7-(4-fluorophenyl)-7-(3-formyl-6-hydroxy-2,4,5-trimethylphenyl)heptanoate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24193Titanium TetrachlorideKatalysatorHCID 6344
Dichloromethane
Lösungsmittel
2×

Versuchsvorschrift

To a solution of methyl (R)-7-(4-fluorophenyl)-7-(2-hydroxy-3,4,6-trimethylphenyl)heptanoate (0.8 g, 2.1 ol) and dichloromethyl methyl ether (0.62 ml) in dichloromethane (10 ml) was added dropwise a solution of titanium tetrachloride (0.76 ml) in dichloromethane (3 ml) under argon atmosphere while maintaining the temperatures of the reaction mixture at a range from -10° C. to -12° C. The reaction mixture was then stirred for 30 minutes at the same temperature range. The reaction mixture was then added to ice-water, which was subjected to extraction with ethyl acetate. The organic layer was washed with water, an aqueous solution of sodium hydrogencarbonate, water and a saturated aqueous saline solution, successively, followed by drying over magnesium sulfate. The solvent was distilled off under reduced pressure. The residue was recrystallized from chloroform/hexane to afford 0.63 g of methyl (R)-7-(4-fluorophenyl)-7-(3-formyl-6-hydroxy-2,4,5-trimethylphenyl)heptanoate. Physico-chemical properties and spectral data of the product were shown in [Table 4].

Aufarbeitung

  1. temperaturewhile maintaining the temperatures of the reaction mixture at a range from -10° C. to -12° C
  2. extractionwas subjected to extraction with ethyl acetate
  3. washThe organic layer was washed with water
  4. dry with materialby drying over magnesium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. customThe residue was recrystallized from chloroform/hexane

Quellen und Nachweise

ORD-Eintrag
ord-a43aaa11313945cfb6464505ea8a4bda
Quelldatensatz
uspto-grants-1994_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05354913

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