1-Butanol → HCID 20095015, compound

HRID 1770176Notes

Reaction equation

HRID 1770176 reaction equation
[CH2:1]([CH:7]1[CH2:15][C:14]2[C:9](=[CH:10][CH:11]=[C:12]([C:16]3[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][N:17]=3)[CH:13]=2)[CH2:8]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[CH2:23](I)[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32].[OH-].[K+].C(O)CCC>CO>[CH2:1]([CH:7]1[CH2:15][C:14]2[C:9](=[CH:10][CH:11]=[C:12]([C:16]3[CH:21]=[CH:20][C:19]([O:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])=[CH:18][N:17]=3)[CH:13]=2)[CH2:8]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

6

Reactant 4

HCID 2631-ButanolHCID 14797Potassium HydroxideHCID 163141-IododecaneHCID 20095008HCID 20095008, compound

Product 1

HCID 20095015HCID 20095015, compoundYield 39.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

0.045 g (0.15 mM) of 2-hexyl-5-(5-hydroxypyridine-2-yl)indan, 0.05 ml (0.23 mM) of decyl iodide, 0.013 g (0.20 mM) of 85%-KOH and 1 ml of n-butanol were mixed and heat-refluxed for 130 minutes under stirring. After the reaction, methanol was added to the reaction mixture, followed by filtration under cooling with ice to obtain an insoluble matter. The insoluble matter was dried and purified by silica gel column chromatography (eluent: toluene/ethyl acetate=100/1), followed by recrystallization from acetone to obtain 0.026 g of 2-hexyl-5-(5-decyloxypyridine-2-yl)indan (Yield: 39.2%). ##STR308##

Workup

  1. temperatureheat-refluxed for 130 minutes
  2. additionwas added to the reaction mixture
  3. filtrationfollowed by filtration
  4. temperatureunder cooling with ice
  5. customto obtain an insoluble matter
  6. customThe insoluble matter was dried
  7. custompurified by silica gel column chromatography (eluent: toluene/ethyl acetate=100/1)
  8. customfollowed by recrystallization from acetone

Sources & evidence

ORD record
ord-ea4434876fa8432e939bd23177ee33a5
Source dataset
uspto-grants-1995_01
Patent number
US05385692

Reaction notes

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