Borane;tetrahydrofuran → (6-Fluoronaphthalen-2-yl)methanol

HRID 333228

Reaktionsgleichung

Reaktionsgleichung von HRID 333228
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([C:12](O)=[O:13])[CH:6]=[CH:5]2.B.C1COCC1>>[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([CH2:12][OH:13])[CH:6]=[CH:5]2

Komponenten

3

Edukt 2

HCID 2723981Borane;tetrahydrofuranHCID 27827886-Fluoro-2-naphthoic acid

Produkt 1

HCID 58954787(6-Fluoronaphthalen-2-yl)methanolAusbeute 82 %

Versuchsvorschrift

To a solution of 6-fluoro-naphthalene-2-carboxylic acid (3.0 g, 15.8 mmol) was added BH3.THF (31.6 mL, 31.6 mmol). The reaction mixture was stirred overnight before being concentrated. To the residue was added diethyl ether (100 mL) and NaOH solution (10 mL). The organic layer was separated, dried and concentrated. The resultant residue was purified by silica gel column chromatography (ethyl acetate/hexane 1:7) to afford (6-fluoro-naphthalen-2-yl)-methanol (2.28 g, 82%).

Aufarbeitung

  1. concentrationbefore being concentrated
  2. additionTo the residue was added diethyl ether (100 mL) and NaOH solution (10 mL)
  3. customThe organic layer was separated
  4. customdried
  5. concentrationconcentrated
  6. customThe resultant residue was purified by silica gel column chromatography (ethyl acetate/hexane 1:7)

Quellen und Nachweise

ORD-Eintrag
ord-590c7face87a4de8b262dc42f079c2d3
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08877975B2

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