Methanol → 3,4-Bis(benzyloxy)-6-ethynylpyridazine

HRID 927061Notes

Reaction equation

HRID 927061 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH2:7]([O:14][C:15]1[N:16]=[N:17][C:18]([C:29]#[C:30][Si](C)(C)C)=[CH:19][C:20]=1[O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.CO>O1CCCC1>[CH2:7]([O:14][C:15]1[N:16]=[N:17][C:18]([C:29]#[CH:30])=[CH:19][C:20]=1[O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 11430Potassium CarbonateHCID 712704503,4-Bis(benzyloxy)-6-((trimethylsilyl)ethynyl)pyridazine2×

Product 1

HCID 866770253,4-Bis(benzyloxy)-6-ethynylpyridazineYield 78.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Potassium carbonate (295 mg, 2.136 mmol), 3,4-bis(benzyloxy)-6-((trimethylsilyl)ethynyl)pyridazine (Intermediate 4; 830 mg, 2.14 mmol) and methanol (10 ml) were added to tetrahydrofuran (5 ml) to produce an orange suspension. The mixture was stirred for 1 hour and then partitioned between brine and ethyl acetate. The organic layer was washed with brine and evaporated before the residue was purified by silica chromatography (eluting with 10-50% ethyl acetate in petrol) to yield 3,4-bis(benzyloxy)-6-ethynylpyridazine (530 mg, 1.68 mmol, 78% yield).

Workup

  1. customto produce an orange suspension
  2. custompartitioned between brine and ethyl acetate
  3. washThe organic layer was washed with brine
  4. customevaporated before the residue
  5. customwas purified by silica chromatography (eluting with 10-50% ethyl acetate in petrol)

Sources & evidence

ORD record
ord-c5c4baa3fe7f4af5ba144661b19f00e3
Source dataset
uspto-grants-2016_03
Patent number
US09290456B2

Reaction notes

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