Sodium Hydroxide → (2,3-Dihydro-[1,4]dioxino[2,3-B]pyridin-6-YL)methanol

HRID 1913435Notes

Reaction equation

HRID 1913435 reaction equation
C([O:4][CH2:5][C:6]1[N:11]=[C:10]2[O:12][CH2:13][CH2:14][O:15][C:9]2=[CH:8][CH:7]=1)(=O)C.[OH-].[Na+]>CO>[O:15]1[C:9]2[C:10](=[N:11][C:6]([CH2:5][OH:4])=[CH:7][CH:8]=2)[O:12][CH2:13][CH2:14]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67407401HCID 67407401, compound

Product 1

HCID 21873716(2,3-Dihydro-[1,4]dioxino[2,3-B]pyridin-6-YL)methanolYield 80%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of (2,3-dihydro-[1,4]dioxino[2,3-b]pyridin-6-yl)methyl acetate (75.0 g, 0.36 mol) in MeOH (500 mL) was added aqueous NaOH (2M, 350 mL, 0.72 mol) dropwise at 0° C. After the addition, the mixture was stirred at room temperature overnight. The solvent was removed in vacuo and the residue was diluted with water (250 mL). The aqueous solution was washed with CH2Cl2 (2×200 mL). The combined organic layers were washed with brine (2×100 mL), dried over anhydrous Na2SO4 and concentrated to yield (2,3-dihydro-[1,4]dioxino[2,3-b]pyridin-6-yl)methanol (48.0 g, 80%) as a grey solid. The crude material was used directly in the next step.

Workup

  1. additionAfter the addition
  2. customThe solvent was removed in vacuo
  3. additionthe residue was diluted with water (250 mL)
  4. washThe aqueous solution was washed with CH2Cl2 (2×200 mL)
  5. washThe combined organic layers were washed with brine (2×100 mL)
  6. dry with materialdried over anhydrous Na2SO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-f7a3dc7a5515453d842dd1510e71cf09
Source dataset
uspto-grants-2013_12
Patent number
US08609680B2

Reaction notes

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