Sodium borohydride → Methyl 4-hydroxytetrahydro-2H-thiopyran-3-carboxylate

HRID 1053962

Reaktionsgleichung

Reaktionsgleichung von HRID 1053962
[O:1]=[C:2]1[CH2:7][CH2:6][S:5][CH2:4][CH:3]1[C:8]([O:10][CH3:11])=[O:9].[BH4-].[Na+]>C1COCC1>[OH:1][CH:2]1[CH2:7][CH2:6][S:5][CH2:4][CH:3]1[C:8]([O:10][CH3:11])=[O:9]

Komponenten

4

Edukt 2

HCID 4311764Sodium borohydrideHCID 10374916Methyl 4-oxothiane-3-carboxylate

Produkt 1

HCID 10012449Methyl 4-hydroxytetrahydro-2H-thiopyran-3-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of methyl 4-oxotetrahydro-2H-thiopyran-3-carboxylate (3.00 g, 17.2 mmol) in THF (57 mL) was stirred at 0° C. Sodium borohydride (1.30 g, 34.4 mmol) was added and the resulting mixture was stirred at ambient temperature for 4 hours. The mixture was thermally stabilized with a water bath and carefully quenched with 1N aqueous HCl. The reaction mixture was then diluted with water and extracted with EtOAc (2×). The combined organic extracts were washed with water, brine, dried over anhydrous Na2SO4, filtered, and concentrated in vacuo to afford the title compound. The residue was carried forward without further purification.

Aufarbeitung

  1. customThe mixture was thermally stabilized with a water bath
  2. customcarefully quenched with 1N aqueous HCl
  3. additionThe reaction mixture was then diluted with water
  4. extractionextracted with EtOAc (2×)
  5. washThe combined organic extracts were washed with water, brine
  6. dry with materialdried over anhydrous Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-94ccdaf0f4834ef28f29f14c32a6f05c
Quelldatensatz
uspto-grants-2016_07
Patentnummer
US09394282B2

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