Formaldehyde → HCID 86760662, compound

HRID 2221103Notes

Reaction equation

HRID 2221103 reaction equation
[Br:1][C:2]1[N:3]=[N:4][C:5]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[CH:6][C:7]=1[CH2:8][CH:9]([C:17](=O)C)[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11].C[Si]([N-][Si](C)(C)C)(C)C.[Li+].C=O>C1COCC1>[Br:1][C:2]1[N:3]=[N:4][C:5]([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)=[CH:6][C:7]=1[CH2:8][C:9](=[CH2:17])[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 2733832Lithium HexamethyldisilazideHCID 86760663HCID 86760663, compound

Product 1

HCID 86760662HCID 86760662, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of compound 5D, (0.160 g, 0.39 mmol) in 3 mL of THF at room temperature under argon was added 0.43 mL (in THF, 0.43 mmol) of 1M lithium bis(trimethylsilyl)amide over 2 min and, after 20 min, powdered, dry paraformaldehyde (0.059 mg, 1.97 mmol). The cooling bath was removed and the reaction mixture was stirred at room temperature for 3 h. The reaction mixture was then quenched with saturated NaCl and extracted twice with dichloromethane. The combined organic extracts were dried over MgSO4, filtered and evaporated under reduced pressure. Purification by silica gel chromatography (7:93 Ether/CH2Cl2) provided the title compound, tert-butyl 2-((3-bromo-6-phenylpyridazin-4-yl)methyl)acrylate (0.142 g, 97%) as a light yellow oil. MS [M+H]+: found 375.

Workup

  1. customThe cooling bath was removed
  2. customThe reaction mixture was then quenched with saturated NaCl
  3. extractionextracted twice with dichloromethane
  4. dry with materialThe combined organic extracts were dried over MgSO4
  5. filtrationfiltered
  6. customevaporated under reduced pressure
  7. customPurification by silica gel chromatography (7:93 Ether/CH2Cl2)

Sources & evidence

ORD record
ord-dbe448d73a9b4479ba9cd7764c35d805
Source dataset
uspto-grants-2008_05
Patent number
US07368458B2

Reaction notes

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