Hydrochloric Acid → methyl (S)-3-benzyloxymethyloxy-2-methylpropionate

HRID 654987Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 654987
[CH3:1][C@@H:2]([CH2:7][OH:8])[C:3]([O:5][CH3:6])=[O:4].C(N(C(C)C)CC)(C)C.[CH2:18]([O:25][CH2:26]Cl)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.Cl>ClCCl.C(OCC)(=O)C>[CH2:18]([O:25][CH2:26][O:8][CH2:7][C@H:2]([CH3:1])[C:3]([O:5][CH3:6])=[O:4])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 81531DiisopropylethylamineHCID 137983Benzyl chloromethyl etherHCID 10192563methyl (2S)-3-hydroxy-2-methylpropanoate

Produkt 1

HCID 14348497methyl (S)-3-benzyloxymethyloxy-2-methylpropionate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Methyl (S)-(+)-2-methyl-3-hydroxypropionate (2.0 g; 16.9 mmole) and diisopropylethylamine (2.2 g; 17.1 mmole) were dissolved in dry dichloromethane (2 ml), and benzyloxymethyl chloride (2.7 g; 17.3 mmole) was dropwise added thereto, followed by stirring for 1 hour. 1N Hydrochloric acid (10 ml) and ethyl acetate (20 ml) were added thereto, and the aqueous layer was extracted with ethyl acetate. The extract was combined with the organic layer, washed with a sodium bicarbonate solution and water and dried over anhydrous magnesium sulfate. After removal of the solvent under reduced pressure, the residue was purified by silica gel column chromatography to give methyl (S)-3-benzyloxymethyloxy-2-methylpropionate.

Aufarbeitung

  1. extractionthe aqueous layer was extracted with ethyl acetate
  2. washwashed with a sodium bicarbonate solution and water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customAfter removal of the solvent under reduced pressure
  5. customthe residue was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-a31efad7e8364d32bd45e1d90163e36e
Quelldatensatz
uspto-grants-1992_07
Patentnummer
US05134231

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