(6-Chloropyridin-3-yl)methanol → HCID 10630706, compound

HRID 2090288Notes

Reaction equation

HRID 2090288 reaction equation
Cl[C:2]1[N:7]=[CH:6][C:5]([CH2:8][OH:9])=[CH:4][CH:3]=1.[O-:10][CH2:11][CH3:12].[Na+]>C(O)C.C(OCC)(=O)C>[CH2:11]([O:10][C:2]1[N:7]=[CH:6][C:5]([CH2:8][OH:9])=[CH:4][CH:3]=1)[CH3:12]

Participants

5

Reactant 2

HCID 177161(6-Chloropyridin-3-yl)methanolHCID 2723922Sodium ethoxide

Product 1

HCID 10630706HCID 10630706, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
95 °C

Procedure

A mixture of (6-chloropyridin-3-yl)methanol (1.4 g, 0.010 mol, Aldrich, Cat. 536016) and sodium ethoxide (3.0 g, 0.044 mol) in ethanol (30 mL) was stirred at 95° C. for 36 hours. The reaction mixture was cooled to r.t., diluted with ethyl acetate, washed with water and brine successively, dried with MgSO4, and concentrated to afford the desired compound. The crude product was directly used in the next step without further purification. LCMS (M+H)+: m/z=154.3.

Workup

  1. temperatureThe reaction mixture was cooled to r.t.
  2. washwashed with water and brine successively
  3. dry with materialdried with MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-cd9f4d7bc02243c99b2210633e597806
Source dataset
uspto-grants-2013_05
Patent number
US08436008B2

Reaction notes

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