Ethanol → (5-[1,3]Dioxolan-2-yl-pyridin-2-yl)-methanol

HRID 78156Notes

Reaction equation

HRID 78156 reaction equation
C(O)C.O1CCCC1.[O:9]1[CH2:13][CH2:12][O:11][CH:10]1[C:14]1[CH:15]=[CH:16][C:17]([CH:20]=[O:21])=[N:18][CH:19]=1.[BH4-].[Na+]>O>[O:9]1[CH2:13][CH2:12][O:11][CH:10]1[C:14]1[CH:15]=[CH:16][C:17]([CH2:20][OH:21])=[N:18][CH:19]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 8028TetrahydrofuranHCID 4311764Sodium borohydrideHCID 592551735-(1,3-Dioxolan-2-yl)picolinaldehyde

Product 1

HCID 59255267(5-[1,3]Dioxolan-2-yl-pyridin-2-yl)-methanolYield 78.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To an ethanol (20 mL) and tetrahydrofuran (20 mL) solution of 5-[1,3]dioxolan-2-yl-pyridine-2-carbaldehyde (1.73 g, 9.66 mmol) described in Manufacturing Example 154-1-3 was added sodium borohydride (731 mg, 19.3 mmol), which was stirred for 25 minutes at room temperature. Water was added to the reaction mixture, which was extracted with ethyl acetate. The organic layer was separated, washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under a reduced pressure, and the residue was purified by silica gel column chromatography (heptane: ethyl acetate=1:2) to obtain the title compound (1.37 g, 78%).

Workup

  1. extractionwas extracted with ethyl acetate
  2. customThe organic layer was separated
  3. washwashed with saturated aqueous sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated under a reduced pressure
  7. customthe residue was purified by silica gel column chromatography (heptane: ethyl acetate=1:2)

Sources & evidence

ORD record
ord-dfd267de48694a61905a161355acc6bc
Source dataset
uspto-grants-2014_09
Patent number
US08841327B2

Reaction notes

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