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

HRID 1880581Notes

Reaction equation

HRID 1880581 reaction equation
F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.[Cl:28][C:29]1[C:30]([C:36](O)=[O:37])=[N:31][C:32]([Cl:35])=[CH:33][CH:34]=1.CCN(C(C)C)C(C)C.[BH4-].[Na+]>C1COCC1>[Cl:28][C:29]1[C:30]([CH2:36][OH:37])=[N:31][C:32]([Cl:35])=[CH:33][CH:34]=1

Participants

6

Reactant 4

HCID 15553ClopyralidHCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 4311764Sodium borohydride

Product 1

HCID 20366200(3,6-Dichloropyridin-2-yl)methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

BOP (1.27 g, 2.9 mmol) was added to a THF (10 mL) solution containing 3,6-dichloropyridine-2-carboxylic acid (0.5 g, 2.6 mmol) and DIEA (0.55 mL, 3.2 mmol). After 5 minutes sodium borohydride (103 mg, 2.7 mmol) was added and the solution stirred at room temperature for 20 minutes. The solution was partitioned between ethyl ether and aqueous 1N HCl. The organic phase was washed with water, brine and dried over MgSO4. The solution was filtered, concentrated and the residue purified by silica gel chromatography using a hexanes/ethyl acetate gradient to give the title compound. LCMS2 1.32 min. (M+H)=178

Workup

  1. customThe solution was partitioned between ethyl ether and aqueous 1N HCl
  2. washThe organic phase was washed with water, brine
  3. dry with materialdried over MgSO4
  4. filtrationThe solution was filtered
  5. concentrationconcentrated
  6. customthe residue purified by silica gel chromatography

Sources & evidence

ORD record
ord-062a8497b14c4f1dbdb2f591f61ea9e0
Source dataset
uspto-grants-2012_11
Patent number
US08318760B2

Reaction notes

Loading…