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

HRID 333228

Reaction equation

HRID 333228 reaction equation
[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

Participants

3

Reactant 2

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

Product 1

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

Procedure

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%).

Workup

  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)

Sources & evidence

ORD record
ord-590c7face87a4de8b262dc42f079c2d3
Source dataset
uspto-grants-2014_11
Patent number
US08877975B2

Linked notes

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