Pyridine → HCID 18753376, compound

HRID 1838272Notes

Reaction equation

HRID 1838272 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]=[N:12][OH:13])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].ClN1C(=O)CCC1=O.N1C=CC=CC=1.[CH2:28]([OH:33])[CH2:29][CH2:30][CH:31]=[CH2:32].C(N(CC)CC)C.C([O-])(O)=O.[Na+]>O1CCCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[CH2:32][CH:31]([CH2:30][CH2:29][CH2:28][OH:33])[O:13][N:12]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

8

Reactant 6

HCID 1049PyridineHCID 8471TriethylamineHCID 131814-Penten-1-OLHCID 16577N-[(3,4-Dimethoxyphenyl)methylidene]hydroxylamineHCID 31398ChlorosuccinimideHCID 516892Sodium Bicarbonate

Product 1

HCID 18753376HCID 18753376, compoundYield 90.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

(3,4-dimethoxyphenyl)(hydroxyimino)methane (1.05 g, 5.801 mmol) was dissolved in 30 mL of tetrahydrofuran under N2. After adding N-chlorosuccinimide (0.93 g, 6.96 mmol) and pyridine (46.9 L, 0.580 mmol) at room temperature, the reaction was continued for 30 min at 60. After cooling to room temperature, 4-pentene-1-ol (0.90 mL, 8.701 mmol) dissolved in 2 mL of tetrahydrofuran was added. Then, after adding triethylamine (0.97 mL, 6.961 mmol) dissolved in 2 mL of tetrahydrofuran, the reaction was continued for 1 hr at 50. When the reaction was completed, saturated NaHCO3 solution was added, and then the same was extracted with ethyl acetate. After drying over anhydrous MgSO4, the crude product was purified by column chromatography on silica gel (hexane/ethyl acetate=1/2, v/v) to obtain 1.38 g (90.6%) of the target compound.

Workup

  1. additionwas added
  2. waitthe reaction was continued for 1 hr at 50
  3. extractionthe same was extracted with ethyl acetate
  4. dry with materialAfter drying over anhydrous MgSO4
  5. customthe crude product was purified by column chromatography on silica gel (hexane/ethyl acetate=1/2

Sources & evidence

ORD record
ord-b6adc6a4ef22477fbd8474d79663a82b
Source dataset
uspto-grants-2004_01
Patent number
US06673800B2

Reaction notes

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