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methyl (S)-lactate → methyl (S)-2-(methoxymethoxy)propionate

HRID 1821145
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1821145
[C:1]([O:6][CH3:7])(=[O:5])[C@H:2]([CH3:4])[OH:3].C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.ClC[C:27]([O:29][CH2:30]OC)=C.C(=O)([O-])O.[Na+]>C1(C(F)(F)F)C=CC=CC=1>[CH3:27][O:29][CH2:30][O:3][C@@H:2]([CH3:4])[C:1]([O:6][CH3:7])=[O:5]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 94386methyl (S)-lactateHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 516892Sodium BicarbonateHCID 106782943-Chloro-2-(methoxymethoxy)prop-1-ene

Produkt 1

HCID 10582920methyl (S)-2-(methoxymethoxy)propionateAusbeute 84 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7368
(Trifluoromethyl)benzene
Lösungsmittel

Versuchsvorschrift

Methyl L-lactate (208 mg, 2 mmol) was dissolved in benzotrifluoride (2.0 mL), pyridinium p-toluenesulfonate (PPTS, 50 mg, 0.2 mmol) was added and then 2-(chloromethyl)-3,5-dioxahexa-1-ene (manufactured by Tokyo Kasei Kogyo Co., Ltd., 327 mg, 2.4 mmol) was added, and the mixture was stirred at room temperature for 24 hrs. Saturated aqueous sodium hydrogencarbonate solution (3 mL) was added to the reaction mixture, and the mixture was extracted with ethyl acetate (4 mL). The organic layer was washed with saturated aqueous sodium hydrogencarbonate solution (2 mL) and dried over anhydrous magnesium sulfate (0.5 g), and the solvent was evaporated under reduced pressure to give methyl (S)-2-(methoxymethoxy)propionate (248 mg, yield 84%).

Aufarbeitung

  1. extractionthe mixture was extracted with ethyl acetate (4 mL)
  2. washThe organic layer was washed with saturated aqueous sodium hydrogencarbonate solution (2 mL)
  3. dry with materialdried over anhydrous magnesium sulfate (0.5 g)
  4. customthe solvent was evaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-5d5db703235044468071285d6242b432
Quelldatensatz
uspto-grants-2009_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07605286B2

Notizen zur Reaktion

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