Sodium hydride → 2-(tert-Butyl)-4-(3-methylbutoxy)-5-chloro-3(2H)-pyridazinone

HRID 381923Notes

Reaction equation

HRID 381923 reaction equation
[CH3:1][CH:2]([CH3:6])[CH2:3][CH2:4][OH:5].[H-].[Na+].[H][H].[C:11]([N:15]1[C:20](=[O:21])[C:19](Cl)=[C:18]([Cl:23])[CH:17]=[N:16]1)([CH3:14])([CH3:13])[CH3:12]>O1CCCC1>[C:11]([N:15]1[C:20](=[O:21])[C:19]([O:5][CH2:4][CH2:3][CH:2]([CH3:6])[CH3:1])=[C:18]([Cl:23])[CH:17]=[N:16]1)([CH3:14])([CH3:12])[CH3:13]

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 31260Isoamyl AlcoholHCID 27822252-Tert-butyl-4,5-dichloro-2,3-dihydropyridazin-3-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 219340142-(tert-Butyl)-4-(3-methylbutoxy)-5-chloro-3(2H)-pyridazinone

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A stirred, room temperature solution of 3-methyl-1-butanol (0.5 mL, 4.52 mmol) in tetrahydrofuran (10 mL) was treated with a 60% oil suspension of sodium hydride (0.24 g, 5.88 mmol). After 5 minutes, hydrogen gas evolution had subsided, so the dichloro-intermediate from Example 330A (1.0 g, 4.52 mmol) was added and the reaction mixture was stirred at room temperature for 20 hours. The reaction was quenched with 10% aqueous citric acid and extracted with ethyl acetate. The organic layer was washed with brine, dried over MgSO4, and filtered. The filtrate was concentrated in vacuo, and the residue was purified by column chromatography (silica gel, 100% hexanes). The title compound was obtained as a pale yellow oil (yield: 0.7 g, 56.7%). 1H NMR (300 MHz, CDCl3) δ 0.95 (d, J=6 Hz, 6H), 1.63 (s, 9H), 1.64 (q, J=6 Hz, 2H), 1.85 (nonet, J=6 Hz, 1H), 4.49 (t, J=6 Hz, 2H), 7.64 (s, 1H). MS (DCI/NH3) m/z 273 (M+H)+, 290 (M+NH4)+.

Workup

  1. additionwas added
  2. customThe reaction was quenched with 10% aqueous citric acid
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated in vacuo
  8. customthe residue was purified by column chromatography (silica gel, 100% hexanes)

Sources & evidence

ORD record
ord-b7632b0858394609b53d3ff2f4a676b1
Source dataset
uspto-grants-2001_10
Patent number
US06307047B1

Reaction notes

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