6-Fluoro-1-indanone → 6-fluoro-2,3-dihydro-1H-inden-1-ol

HRID 237265Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 237265
[F:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][C:8]2=[O:11])=[CH:4][CH:3]=1.[BH4-].[Na+]>ClCCCl.CO>[F:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][CH:8]2[OH:11])=[CH:4][CH:3]=1

Komponenten

5

Edukt 2

HCID 15194646-Fluoro-1-indanoneHCID 4311764Sodium borohydride

Produkt 1

HCID 613834996-fluoro-2,3-dihydro-1H-inden-1-olAusbeute 97,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 111,2-DichloroethaneLösungsmittelHCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of 6-fluoro-indan-1-one (0.50 g, 3.3 mmol) in DCE (10 mL) and MeOH (10 mL) was added NaBH4 (0.25 g, 6.6 mmol). After 30 min the reaction was quenched with H2O (10 mL) and extracted with CH2Cl2 (3×20 mL). The organic layers were combined and dried to give the title compound (0.49 g, 97%). MS (ESI): mass calcd. for C9H7FO, 150.1; m/z found, 151.4 [M+H]+. 1H NMR (CDCl3): 7.23-7.13 (m, 1H), 7.09 (dd, J=8.6, 2.5 Hz, 1H), 6.99-6.90 (m, 1H), 5.21 (t, J=6.3 Hz, 1H), 3.13-2.91 (m, 1H), 2.85-2.68 (m, 1H), 2.63-2.44 (m, 1H), 2.09-1.74 (m, 2H).

Aufarbeitung

  1. customAfter 30 min the reaction was quenched with H2O (10 mL)
  2. extractionextracted with CH2Cl2 (3×20 mL)
  3. customdried

Quellen und Nachweise

ORD-Eintrag
ord-644ed4a1df314c70b61439dc48c28ab4
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08642583B2

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