Methanol → Dipyridin-3-ylmethanol

HRID 2278169Notes

Reaction equation

HRID 2278169 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]([C:9]2[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=2)=[O:8])[CH:2]=1.CO.[BH4-].[Na+]>C(Cl)Cl>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH:7]([C:9]2[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=2)[OH:8])[CH:2]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 298471Di-3-pyridinylmethanoneHCID 4311764Sodium borohydride

Product 1

HCID 11309949Dipyridin-3-ylmethanol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A round bottom flask was charged with di(pyridin-3-yl)methanone (500 mg, 2.72 mmol), MeOH (30 mL), and CH2Cl2 (15 mL) and cooled to 0° C. NaBH4 (51 mg, 1.35 mmol) was added in one portion. The solution was stirred for 1 h at 0° C. and quenched with 1N NaOH and the reaction was extracted with CH2Cl2 (3×). The organic layers were combined, dried over Na2SO4 and concentrated under reduced pressure. Crude di(pyridin-3-yl)methanol (505 mg, 100%) was used in the next step without further purification. 1H NMR 400 MHz (CDCl3) δ 8.32 (s, 2H), 8.24 (d, J=4.8 Hz, 2H), 7.47 (d, J=7.9 Hz, 2H), 7.09-7.01 (m, 2H), 5.67 (s, 1H).

Workup

  1. customquenched with 1N NaOH
  2. extractionthe reaction was extracted with CH2Cl2 (3×)
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customCrude di(pyridin-3-yl)methanol (505 mg, 100%) was used in the next step without further purification

Sources & evidence

ORD record
ord-2aaaf81d583c426fb896c04c1a7c63f3
Source dataset
uspto-grants-2015_09
Patent number
US09133148B2

Reaction notes

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