Benzyl Bromide → (3-(Benzyloxy)pyridin-2-yl)methanol

HRID 1170910Notes

Reaction equation

HRID 1170910 reaction equation
[OH:1][CH2:2][C:3]1[C:8]([OH:9])=[CH:7][CH:6]=[CH:5][N:4]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:16](Br)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>CC(C)=O>[CH2:16]([O:9][C:8]1[C:3]([CH2:2][OH:1])=[N:4][CH:5]=[CH:6][CH:7]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 841693-Hydroxypyridine-2-methanol

Product 1

HCID 13217540(3-(Benzyloxy)pyridin-2-yl)methanolYield 66%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

2-hydroxymethyl-3-hydroxypyridine (100.3 g, 620.7 mmol) was dissolved in acetone (1 L). Potassium carbonate (180 g, 1.3 mol) was added followed by benzyl bromide (127 g, 745 mmol). The mixture was heated at reflux for 48 hours. The resultant mixture was cooled to room temperature and filtered through celite. The filter cake was washed with acetone (1 L). The combined filtrate was concentrated in vacuo to provide an orange oil. This oil was purified by silica gel column chromatography using 10-40% ethyl acetate/hexanes as eluant. The resultant tan solid was recrystallized from hexanes to provide the product (88.2 g, 66% yield). 1H NMR (400 MHz, CDCl3) δ 8.2 (t, 1H), 7.4 (m, 5H), 7.15 (d, 2H), 5.1 (s, 2H), 4.8 (d, 2H), 4.3 (t, 1H).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 48 hours
  3. filtrationfiltered through celite
  4. washThe filter cake was washed with acetone (1 L)
  5. concentrationThe combined filtrate was concentrated in vacuo
  6. customto provide an orange oil
  7. customThis oil was purified by silica gel column chromatography
  8. customThe resultant tan solid was recrystallized from hexanes

Sources & evidence

ORD record
ord-e0c6965db49d4b1297013ca50b0985d2
Source dataset
uspto-grants-2010_11
Patent number
US07829572B2

Reaction notes

Loading…