Tetrahydrofurfuryl alcohol → [1,4]Benzodioxino[2,3-c]pyridazin-3-ylmethanol

HRID 1503208Notes

Reaction equation

HRID 1503208 reaction equation
C[O:2][C:3]([C:5]1[N:10]=[N:9][C:8]2[O:11][C:12]3[CH:18]=[CH:17][CH:16]=[CH:15][C:13]=3[O:14][C:7]=2[CH:6]=1)=O.O1CCCC1CO.[BH4-].[Na+]>O>[N:9]1[C:8]2[O:11][C:12]3[CH:18]=[CH:17][CH:16]=[CH:15][C:13]=3[O:14][C:7]=2[CH:6]=[C:5]([CH2:3][OH:2])[N:10]=1

Participants

5

Reactant 3

HCID 7360Tetrahydrofurfuryl alcoholHCID 4311764Sodium borohydrideHCID 117695404Methyl[1,4]benzodioxino[2,3-c]pyridazine-3-carboxylate

Product 1

HCID 117691161[1,4]Benzodioxino[2,3-c]pyridazin-3-ylmethanolYield 66.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To methyl[1,4]benzodioxino[2,3-c]pyridazine-3-carboxylate (950 mg) was added a mixed solvent of tetrahydrofuran-methanol (1:1) (20 ml), and the mixture was stirred under ice-cooling. To the mixture was added sodium borohydride (450 mg), and the mixture was stirred at 0° C. for 2 hr. Water was added and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was concentrated under reduced pressure, and the residue was washed with water to give [1,4]benzodioxino[2,3-c]pyridazin-3-ylmethanol (560 mg).

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred at 0° C. for 2 hr
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationThe solvent was concentrated under reduced pressure
  7. washthe residue was washed with water

Sources & evidence

ORD record
ord-e2de03019b254c189317c4774b40a54c
Source dataset
uspto-grants-2015_12
Patent number
US09212147B2

Reaction notes

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