Sodium Methoxide → HCID 20095053, compound

HRID 1770164Notes

Reaction equation

HRID 1770164 reaction equation
Cl.[CH2:2]([CH:10]1[CH2:18][C:17]2[C:12](=[CH:13][CH:14]=[C:15]([C:19](=[NH:21])[NH2:20])[CH:16]=2)[CH2:11]1)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9].C[O-].[Na+]>CO>[CH2:2]([CH:10]1[CH2:18][C:17]2[C:12](=[CH:13][CH:14]=[C:15]([C:19]3[N:20]=[CH:13][C:12]([CH2:11][CH2:10][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9])=[CH:17][N:21]=3)[CH:16]=2)[CH2:11]1)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 20095057HCID 20095057, compound

Product 1

HCID 20095053HCID 20095053, compoundYield 108.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1.00 g (3.24 mM) of 2-octyl-5-amidinoindan hydrochloride, 0.40 g (7.40 mM) of sodium methylate, 0.82 g (3.43 mM) of α-octyloxy-β-dimethylaminoacrolein and 15 ml of methanol were placed in a 30 ml-round bottomed flask, followed by refluxing for 10.5 hours under stirring. After the reaction, the reaction mixture was left standing in a refrigerator for 2 days to precipitate a crystal. The crystal was recovered by filtration and dissolved in toluene, followed by drying with anhydrous sodium sulfate and filtration. The filtrate was evaporated to obtain a residue. The residue was purified by silica gel column chromatography (eluent: toluene/ethyl acetate=100/1) and recrystallized from a mixture solvent (toluene/methanol) to obtain 0.79 g of 2-octyl-5-(5-decylpyrimidine-2-yl)indan (Yield: 54.4%). ##STR151##

Workup

  1. temperatureby refluxing for 10.5 hours
  2. customAfter the reaction
  3. waitthe reaction mixture was left
  4. customto precipitate a crystal
  5. filtrationThe crystal was recovered by filtration
  6. dissolutiondissolved in toluene
  7. dry with materialby drying with anhydrous sodium sulfate and filtration
  8. customThe filtrate was evaporated
  9. customto obtain a residue
  10. customThe residue was purified by silica gel column chromatography (eluent: toluene/ethyl acetate=100/1)
  11. customrecrystallized from a mixture solvent (toluene/methanol)

Sources & evidence

ORD record
ord-5e9bdec744a14e7fb983ded191b0eb81
Source dataset
uspto-grants-1995_01
Patent number
US05385692

Reaction notes

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