Sodium borohydride → (5-(Phenylethynyl)pyridin-3-yl)methanol

HRID 2362427Notes

Reaction equation

HRID 2362427 reaction equation
[C:1]1([C:7]#[C:8][C:9]2[CH:10]=[N:11][CH:12]=[C:13]([CH:16]=2)[CH:14]=[O:15])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[BH4-].[Na+]>C(O)C>[C:1]1([C:7]#[C:8][C:9]2[CH:16]=[C:13]([CH2:14][OH:15])[CH:12]=[N:11][CH:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 10679834HCID 10679834, compound

Product 1

HCID 67047855(5-(Phenylethynyl)pyridin-3-yl)methanol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

To a suspension of 5-(Phenylethynyl)nicotinaldehyde (7.0 g, 33.8 mmol) in ethanol (150 mL), immersed in a room temperature bath to moderate any potential exotherm, was added sodium borohydride (0.639 g, 16.9 mmol) in one portion. After 30 min at room temperature, the reaction was cooled to 0° C. and quenched by the cautious addition of saturated ammonium chloride. The reaction was concentrated and partitioned between water and ether. The aqueous was extracted with ether (2×). The organics were washed with brine, dried over magnesium sulfate, and concentrated to give a faint yellow solid. Material was used without purification. 1H NMR (CDCl3) δ: 8.39-8.81 (m, 2H), 7.88 (s, 1H), 7.51-7.61 (m, 2H), 7.34-7.44 (m, 3H), 4.77 (s, 2H), 3.21 (br. s., 1H). 13C NMR (CDCl3) δ: 151.1, 147.1, 137.3, 131.8, 129.0, 128.6, 122.5, 93.0, 85.9, 62.3. Mass spec.: 210.1 (MH)+.

Workup

  1. customimmersed in a room temperature
  2. customquenched by the cautious addition of saturated ammonium chloride
  3. concentrationThe reaction was concentrated
  4. custompartitioned between water and ether
  5. extractionThe aqueous was extracted with ether (2×)
  6. washThe organics were washed with brine
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated
  9. customto give a faint yellow solid
  10. customMaterial was used without purification

Sources & evidence

ORD record
ord-cac65289b79e4b53b3fe51a56be6e757
Source dataset
uspto-grants-2014_04
Patent number
US08691821B2

Reaction notes

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