Hydrochloric Acid → HCID 66771287, Verbindung

HRID 1045662Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1045662
[BH4-].[Na+].[Cl:3][CH2:4][C:5]([NH:7][CH:8]1[C:17](=[O:18])[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[O:10][CH2:9]1)=[O:6].O.Cl>CO>[Cl:3][CH2:4][C:5]([NH:7][C@H:8]1[C@H:17]([OH:18])[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[O:10][CH2:9]1)=[O:6]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 4311764Sodium borohydrideHCID 57869938HCID 57869938, Verbindung

Produkt 1

HCID 66771287HCID 66771287, VerbindungAusbeute 99,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

Sodium borohydride (0.9 g, 23.8 mol) was added to a solution of 2-chloro-N-(4-oxo-chroman-3-yl)-acetamide (3.5 g, 14.6 mmol) in methanol (30 ml). When the reaction was complete (checked by thin layer chromatography), excess reagent was decomposed by the addition of water and pH was adjusted to 5-6 with 3N aqueous hydrochloric acid. The solution was partitioned between water and chloroform. The organic layer was washed with brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent; 5-10% methanol in chloroform) to afford 2-chloro-N-((3RS,4RS)-trans-4-hydroxychroman-3-yl)-acetamide (3.5 g, 14.5 mmol, 99%) as white crystals.

Aufarbeitung

  1. customThe solution was partitioned between water and chloroform
  2. washThe organic layer was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (eluent; 5-10% methanol in chloroform)

Quellen und Nachweise

ORD-Eintrag
ord-69d65c9f4ef04b95adfe0e570026c7e5
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08569294B2

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