Water → HCID 89581124, compound

HRID 1501248Notes

Reaction equation

HRID 1501248 reaction equation
[C:1]([C:4]1[N:9]=[N:8][C:7]([C:10]([O:12][CH3:13])=[O:11])=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[BH4-].[Na+].C(OCC)(=O)C.O>CO>[OH:3][CH:1]([C:4]1[N:9]=[N:8][C:7]([C:10]([O:12][CH3:13])=[O:11])=[CH:6][CH:5]=1)[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 4311764Sodium borohydrideHCID 89580815HCID 89580815, compound

Product 1

HCID 89581124HCID 89581124, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
-70 °C

Procedure

To a solution of methyl 6-acetylpyridazine-3-carboxylate (0.8 g, 4.4 mmol) in methanol (30 mL) was added sodium borohydride (340 mg, 8.8 mmol) at −70° C. under nitrogen gas protected. The mixture solution was stirred for 3 hours at −70° C., then poured into ethyl acetate (50 mL) and water (50 mL). Separated organic layer was dried over sodium sulfate and concentrated to dry. The residue was purified by column chromatography (silica-gel, petroleum/ethyl acetate=5:) to give methyl 6-(1-hydroxyethyl)pyridazine-3-carboxylate as a white solid (200 mg, 25%). 1H NMR (300 MHz, CDCl3): δ 8.22 (d, J=9 Hz, 1H), 7.93 (d, J=9 Hz, 1H), 5.07 (m, 1H), 3.96 (s, 3H), 1.46 (d, J=6 Hz, 3H).

Workup

  1. dry with materialSeparated organic layer was dried over sodium sulfate
  2. concentrationconcentrated
  3. customto dry
  4. customThe residue was purified by column chromatography (silica-gel, petroleum/ethyl acetate=5:)

Sources & evidence

ORD record
ord-6917e6736bc94842b9a1c0d771997ccf
Source dataset
uspto-grants-2015_12
Patent number
US09206128B2

Reaction notes

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