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Hydrochloric Acid → 6,7-Dihydroxy-4-thiaoctanoic acid methyl ester

HRID 1720803
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1720803
[O:1]1[CH2:6][CH:2]1[CH:3]([OH:5])[CH3:4].Cl.[SH:8][CH2:9][CH2:10][C:11]([O:13][CH3:14])=[O:12]>C(Cl)Cl.C[O-].[Na+]>[CH3:14][O:13][C:11](=[O:12])[CH2:10][CH2:9][S:8][CH2:6][CH:2]([OH:1])[CH:3]([OH:5])[CH3:4]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 18050Methyl 3-mercaptopropionateHCID 115934311-(Oxiran-2-yl)ethan-1-ol

Produkt 1

HCID 106798886,7-Dihydroxy-4-thiaoctanoic acid methyl esterAusbeute 55 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittel
HCID 10942334
Sodium Methoxide
Lösungsmittel

Versuchsvorschrift

To a solution of 3,4-epoxy-2-butanol as obtained in Reference Example 43 (1.13 g) in methylene chloride (4 ml), methyl 3-mercaptopropionate (2.00 ml) and sodium methylate (260 μl) were added under ice cooling conditions, followed by stirring at room temperature for 1 day. To the reaction mixture, 1N hydrochloric acid was added, and the mixture was extracted with ethyl acetate; the solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography (ethyl acetate:hexane=2:1) to yield the title compound (1.47 g, yield 55%) as a colorless oily substance.

Aufarbeitung

  1. additionwere added under ice cooling conditions
  2. extractionthe mixture was extracted with ethyl acetate
  3. distillationthe solvent was distilled off under reduced pressure
  4. customThe resulting residue was purified by silica gel column chromatography (ethyl acetate:hexane=2:1)

Quellen und Nachweise

ORD-Eintrag
ord-5de6a0153ba54a78b04b9d334bd4a2b7
Quelldatensatz
uspto-grants-1996_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05506267

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