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

HRID 1691362Notes

Reaction equation

HRID 1691362 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-1f44bfde3826424e98398af0d5da494c
Source dataset
uspto-grants-2012_04
Patent number
US08153662B2

Reaction notes

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