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

HRID 1694110Notes

Reaction equation

HRID 1694110 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-cf0496c23ce64a74979ce9513871c1b0
Source dataset
uspto-grants-2012_04
Patent number
US08158657B2

Reaction notes

Loading…