Water → 7-Methyl-2,3-dihydro-[1,4]dioxino[2,3-c]pyridine

HRID 1038592Notes

Reaction equation

HRID 1038592 reaction equation
O[CH2:2][CH2:3][O:4][C:5]1[CH:10]=[C:9]([CH3:11])[N:8]=[CH:7][C:6]=1[OH:12].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)(C)C)=O)=NC(OC(C)(C)C)=O.O>O1CCCC1>[CH3:11][C:9]1[N:8]=[CH:7][C:6]2[O:12][CH2:2][CH2:3][O:4][C:5]=2[CH:10]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11776TriphenylphosphineHCID 97268Di-tert-butyl azodicarboxylateHCID 665990334-(2-Hydroxyethoxy)-6-methylpyridin-3-ol

Product 1

HCID 233941467-Methyl-2,3-dihydro-[1,4]dioxino[2,3-c]pyridineYield 272.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

After drying 4-(2-hydroxyethoxy)-6-methylpyridin-3-ol (714 mg, 4.22 mmol) and triphenylphosphine (1.66 g, 6.33 mmol) with a vacuum pump, the resultant was dissolved in tetrahydrofuran (42 mL), added di-tert-butyl azodicarboxylate (DBAD) (1.46 g, 6.33 mmol) under ice-cold conditions, and the mixture was stirred at room temperature overnight. Under ice-cold conditions, the reaction solution was added water, and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate, and concentrated in vacuo. The obtained residue was purified by silica-gel column chromatography (hexane/acetone, chloroform/methanol). The title compound (1.74 g (yield >100%)) was obtained as a white solid as a crude product.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe obtained residue was purified by silica-gel column chromatography (hexane/acetone, chloroform/methanol)

Sources & evidence

ORD record
ord-7ac0bb0f83a240b2bbc036f6d1e194bd
Source dataset
uspto-grants-2013_10
Patent number
US08551985B2

Reaction notes

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