Sodium Hydroxide → (3-Methyl-4-(2-(2-propyl-1,3-dioxolan-2-yl)ethoxy)pyridin-2-yl)methanol

HRID 31577Notes

Reaction equation

HRID 31577 reaction equation
C([O:4][CH2:5][C:6]1[C:11]([CH3:12])=[C:10]([O:13][CH2:14][CH2:15][C:16]2([CH2:21][CH2:22][CH3:23])[O:20][CH2:19][CH2:18][O:17]2)[CH:9]=[CH:8][N:7]=1)(=O)C.[OH-].[Na+]>CO>[CH3:12][C:11]1[C:6]([CH2:5][OH:4])=[N:7][CH:8]=[CH:9][C:10]=1[O:13][CH2:14][CH2:15][C:16]1([CH2:21][CH2:22][CH3:23])[O:20][CH2:19][CH2:18][O:17]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 59792410(3-Methyl-4-(2-(2-propyl-1,3-dioxolan-2-yl)ethoxy)pyridin-2-yl)methyl acetate

Product 1

HCID 59792407(3-Methyl-4-(2-(2-propyl-1,3-dioxolan-2-yl)ethoxy)pyridin-2-yl)methanolYield 85%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The (3-methyl-4-(2-(2-propyl-1,3-dioxolan-2-yl)ethoxy)pyridin-2-yl)methyl acetate (1.19 g, 3.68 mmol) obtained in the step (3d) was mixed with a 1N aqueous sodium hydroxide solution (5 ml) and methanol (10 ml). The mixture was stirred at room temperature for 3 hours and concentrated under reduced pressure. The residue was suspended in tetrahydrofuran and sodium sulfate was added to the suspension, and filtered. The filtrate was concentrated under reduced pressure. The residue was dissolved in a solution mixture containing heptane and ethyl acetate at a ratio of 2:1 and subjected to silica gel column chromatography (elution solvent: n-heptane/ethyl acetate=2/1) to obtain the title compound (0.88 g, 85%) as a colorless oil.

Workup

  1. concentrationconcentrated under reduced pressure
  2. additionsodium sulfate was added to the suspension
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. dissolutionThe residue was dissolved in a solution mixture
  6. additioncontaining heptane and ethyl acetate at a ratio of 2:1
  7. washsubjected to silica gel column chromatography (elution solvent: n-heptane/ethyl acetate=2/1)

Sources & evidence

ORD record
ord-0dd8fd1d24ae4fbca4c0a7efb65ca574
Source dataset
uspto-grants-2008_09
Patent number
US07425634B2

Reaction notes

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