Potassium Hydroxide → HCID 20095033, compound

HRID 1770168Notes

Reaction equation

HRID 1770168 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]([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].[OH-].[K+].C1(C)C=CC(S(O[CH2:37][CH:38]([F:45])[CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH3:44])(=O)=O)=CC=1>C(O)CCC>[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][CH2:37][CH:38]([F:45])[CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH3:44])=[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

5

Reactant 3

HCID 14797Potassium HydroxideHCID 14297706HCID 14297706, compoundHCID 20095062HCID 20095062, compound

Product 1

HCID 20095033HCID 20095033, compoundYield 66.4%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

1.0 g (3.01 mM) of 2-octyl-5-(5-hydroxypyrimidine-2-yl)indan, 0.24 g (3.6 mM) of 85%-KOH, 0.91 g (3.01 mM) of 2-fluorooctyl p-toluenesulfonate and 20 ml of butanol was placed in a 50 ml-round bottomed flask and heat-refluxed for 7 hours under stirring. After the reaction, the reaction mixture was poured into ice water and the insoluble matter was recovered by filtration, followed by washing with methanol. The resultant insoluble matter was purified by silica gel column chromatography (eluent: toluene) and recrystallized from a mixture solvent (toluene/methanol) to obtain 0.87 g of 2-octyl-5-[5-(2-fluorooctyloxy)pyrimidine-2-yl]indan (Yield: 66.4%). ##STR297##

Workup

  1. temperatureheat-refluxed for 7 hours
  2. customAfter the reaction
  3. filtrationthe insoluble matter was recovered by filtration
  4. washby washing with methanol
  5. customThe resultant insoluble matter was purified by silica gel column chromatography (eluent: toluene)
  6. customrecrystallized from a mixture solvent (toluene/methanol)

Sources & evidence

ORD record
ord-77049b58321f4e9a998891477c60add6
Source dataset
uspto-grants-1995_01
Patent number
US05385692

Reaction notes

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