2-Benzyl-5-[1,3]dioxolan-2-yl-pyridine → 6-Benzyl-pyridine-3-carbaldehyde

HRID 1694210Notes

Reaction equation

HRID 1694210 reaction equation
[CH2:1]([C:8]1[CH:13]=[CH:12][C:11]([CH:14]2OCC[O:15]2)=[CH:10][N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>Cl>[CH2:1]([C:8]1[N:9]=[CH:10][C:11]([CH:14]=[O:15])=[CH:12][CH:13]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 1

HCID 592551082-Benzyl-5-[1,3]dioxolan-2-yl-pyridine

Product 1

HCID 216983476-Benzyl-pyridine-3-carbaldehydeYield 79.4%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
100 °C

Procedure

2-Benzyl-5-[1,3]dioxolan-2-yl-pyridine (7.3 g, 30 mmol) described in Manufacturing Example 210-1-3 and 2 N hydrochloric acid (100 mL) were stirred for 15 minutes at 100° C. The reaction solution was cooled to room temperature and partitioned into ethyl acetate and a 5 N sodium hydroxide solution (40 mL). The organic layer was separated, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under a reduced pressure to obtain the title compound (4.7 g, 79%).

Workup

  1. temperatureThe reaction solution was cooled to room temperature
  2. custompartitioned into ethyl acetate
  3. customThe organic layer was separated
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated under a reduced pressure

Sources & evidence

ORD record
ord-36eb05578039421cab9050ad845b13b0
Source dataset
uspto-grants-2012_04
Patent number
US08158657B2

Reaction notes

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