Hydrochloric Acid → HCID 20095062, compound

HRID 1770162Notes

Reaction equation

HRID 1770162 reaction equation
[CH2:1]([CH:9]1[CH2:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([C:18]3[N:23]=[CH:22][C:21]([O:24]CC)=[CH:20][N:19]=3)[CH:15]=2)[CH2:10]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[OH-].[Na+].C(O)COCCO.Cl>O>[CH2:1]([CH:9]1[CH2:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([C:18]3[N:23]=[CH:22][C:21]([OH:24])=[CH:20][N:19]=3)[CH:15]=2)[CH2:10]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8117Diethylene GlycolHCID 14798Sodium HydroxideHCID 20095036HCID 20095036, compound

Product 1

HCID 20095062HCID 20095062, compoundYield 89.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

0.5 g (1.42 mM) of 2-octyl-5-(5-ethoxypyrimidine-2-yl)indan, 1.0 g (25 mM) of NaOH and 10 ml of diethylene glycol were mixed and refluxed for 3 hours under stirring. After the reaction, the reaction mixture was poured into water and acidified with HCl to precipitate a crystal. The crystal was recovered by filtration and washed with water. The resultant crystal was dissolved in toluene and washed with water, followed by drying with anhydrous sodium sulfate and distilling-off of the solvent to obtain a residue. The residue was purified by silica gel column chromatography (eluent: toluene/ethyl acetate=1/10) to obtain 0.41 g of 2-octyl-5-(5-hydroxypyrimidine-2-yl)indan (Yield: 89.0%).

Workup

  1. temperaturerefluxed for 3 hours
  2. customAfter the reaction
  3. customto precipitate a crystal
  4. filtrationThe crystal was recovered by filtration
  5. washwashed with water
  6. dissolutionThe resultant crystal was dissolved in toluene
  7. washwashed with water
  8. dry with materialby drying with anhydrous sodium sulfate and distilling-off of the solvent
  9. customto obtain a residue
  10. customThe residue was purified by silica gel column chromatography (eluent: toluene/ethyl acetate=1/10)

Sources & evidence

ORD record
ord-09efc3800e3f4f9f980dfa670eedadba
Source dataset
uspto-grants-1995_01
Patent number
US05385692

Reaction notes

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