Pyridazine → HCID 57803299, compound

HRID 2103365Notes

Reaction equation

HRID 2103365 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][N:2]=1.CC1(C)CCCC(C)(C)N1.[Li].[O:18]1[C:22]2([CH2:27][CH2:26][C:25](=[O:28])[CH2:24][CH2:23]2)[O:21][CH2:20][CH2:19]1>C1COCC1>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:25]2([OH:28])[CH2:26][CH2:27][C:22]3([O:21][CH2:20][CH2:19][O:18]3)[CH2:23][CH2:24]2)[N:2]=1

Participants

5

Reactant 3

HCID 9259PyridazineHCID 5674151,4-Dioxaspiro[4.5]decan-8-oneHCID 5741988838227-87-1

Product 1

HCID 57803299HCID 57803299, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of pyridazine (17.7 mmol, 1.28 mL) in THF (60 mL) was added lithium 2,2,6,6-tetramethylpiperidine (71 mmol, 10 g) at −78° C. The reaction was then stirred for 6 min and 1,4-dioxa-spiro[4.5]decan-8-one (71 mmol, 11 g) was added. The reaction was stirred for 5 h at −78° C. at which point the reaction was quenched using a solution of ethanol, hydrochloric acid and THF (30 mL, 1:1:1). The resulting solution was extracted using EtOAc. The organic layers were combined, dried over MgSO4 and concentrated. The residue was purified using flash chromatography to afford the desired alcohol (44%, 1.84 g). MS (M+H)+237.1.

Workup

  1. stirringThe reaction was stirred for 5 h at −78° C. at which
  2. customwas quenched
  3. extractionThe resulting solution was extracted
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customThe residue was purified

Sources & evidence

ORD record
ord-1c2c36685451482cb47fe6daee09f198
Source dataset
uspto-grants-2009_08
Patent number
US07576089B2

Reaction notes

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