Water → (2,6-Dichloropyridin-3-yl)methanol

HRID 252132Notes

Reaction equation

HRID 252132 reaction equation
[Cl:1][C:2]1[N:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:3]=1[C:4](O)=[O:5].B.O1CCCC1.O.C(=O)([O-])[O-].[K+].[K+]>O1CCCC1.C(OCC)(=O)C>[Cl:1][C:2]1[C:3]([CH2:4][OH:5])=[CH:7][CH:8]=[C:9]([Cl:11])[N:10]=1

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 8540472,6-Dichloronicotinic acidHCID 2723981Borane;tetrahydrofuran

Product 1

HCID 12259932(2,6-Dichloropyridin-3-yl)methanolYield 94.5%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

Dissolve 2,6-dichloronicotinic acid (1000 mg, 5.21 mmol) in anhydrous tetrahydrofuran (5 mL). Cool to 0° C. Add borane-tetrahydrofuran complex (7.82 mL, 7.82 mmol, 1.0 M in tetrahydrofuran) slowly. Stir the mixture at room temperature overnight. Add water (1 mL) and potassium carbonate, stir for 2 hours, filter and concentrate to give a residue. Chromatograph the residue on silica gel eluting with 10:90 to 20:80 ethyl acetate:hexanes to give (2,6-dichloropyridin-3-yl)-methanol (876 mg, 94%). 1H NMR (400 MHz, MeOH-d4) δ 7.96 (d, 1H, J=8.0 Hz), 7.45 (d, 1H, J=8.0 Hz), 4.64 (s, 2H).

Workup

  1. filtrationfilter
  2. concentrationconcentrate
  3. customto give a residue

Sources & evidence

ORD record
ord-306933712d85454c847ca94bba752dda
Source dataset
uspto-grants-2011_01
Patent number
US07868014B2

Reaction notes

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