Sodium borohydride → 2-Chloro-1-(6-fluorochroman-2-yl)ethanol

HRID 2423262Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2423262
[Cl:1][CH2:2][C:3]([CH:5]1[CH2:14][CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([F:15])[CH:11]=2)[O:6]1)=[O:4].[BH4-].[Na+]>C(O)C.O.ClCCl>[Cl:1][CH2:2][CH:3]([CH:5]1[CH2:14][CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([F:15])[CH:11]=2)[O:6]1)[OH:4]

Komponenten

6

Edukt 2

HCID 4311764Sodium borohydrideHCID 167553872-chloro-1-(6-fluoro-3,4-dihydro-2H-chromen-2-yl)ethanone

Produkt 1

HCID 672431242-Chloro-1-(6-fluorochroman-2-yl)ethanolAusbeute 70 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A solution under stirring of 2-chloro-1-(6-fluoro-3,4-dihydro-2H-chromen-2-yl)ethanone (0.33 g, 1.28 mmol, 88.4 A %) in ethanol (2.5 ml) was cooled to 0° C. under nitrogen. NaBH4 (60.1 mg, 1.59 mmol) was added to the solution and the reaction mixture stirred for 2 hours. After checking that the starting product had disappeared by GC, the mixture was diluted with demi water (7 ml) and dichloromethane (7 ml) and the phases separated. The organic stratum was dried under anhydrous sodium sulphate, filtered and concentrated under vacuum to give raw 2-chloro-1-(6-fluoro-3,4-dihydro-2H-chromen-2-yl) ethanol as a mixture of diastereoisomers 54:46 (0.30 g, 70% yield, 67.9 A %).

Aufarbeitung

  1. customthe phases separated
  2. customThe organic stratum was dried under anhydrous sodium sulphate
  3. filtrationfiltered
  4. concentrationconcentrated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-63c947e7ab5145d2ab3af2f0f34bffe0
Quelldatensatz
uspto-grants-2011_06
Patentnummer
US07960572B2

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