Sodium Methoxide → (5-Chloropyridin-2-yl)methanol

HRID 1044419Notes

Reaction equation

HRID 1044419 reaction equation
C[O-].[Na+].C([O:12][CH2:13][C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][N:15]=1)(=O)C1C=CC=CC=1>CO>[Cl:20][C:17]1[CH:18]=[CH:19][C:14]([CH2:13][OH:12])=[N:15][CH:16]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 58580279HCID 58580279, compound

Product 1

HCID 20537893(5-Chloropyridin-2-yl)methanolYield 59%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium methoxide (1M in MeOH) (0.162 mL, 0.162 mmol) was added to a solution of (5-chloropyridin-2-yl)methyl benzoate Part C (200 mg, 0.808 mmol) in MeOH (47.5 mL) and stirred at RT for 2.0 h. The solvent was removed in vacuo and the crude product was subjected to flash chromatography (silica gel/DCM-MeOH 100:0 to 90:10 gradient) to afford (5-chloropyridin-2-yl)methanol 16D (68 mg, 59% yield) as an off-white solid. LC-MS, [M+H]+=144. 1H NMR (400 MHz, DMSO) δ 8.51 (1H, d, J=2.2 Hz), 7.91 (1H, dd, J=8.4, 2.6 Hz), 7.49 (1H, d, J=8.4 Hz), 5.53 (1H, t, J=5.9 Hz), 4.54 (2H, d, J=6.2 Hz). HPLC-Method 8; 0.76 min.

Workup

  1. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-f67a7bfcce0c440d8155c81c562a1657
Source dataset
uspto-grants-2013_10
Patent number
US08563583B2

Reaction notes

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