Potassium Hydroxide → HCID 20095004, compound

HRID 1770158Notes

Reaction equation

HRID 1770158 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]([C:24]4[CH:29]=[CH:28][C:27]([OH:30])=[CH:26][CH:25]=4)=[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[CH2:43][CH:44]([F:51])[CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH3:50])(=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]([C:24]4[CH:29]=[CH:28][C:27]([O:30][CH2:43][CH:44]([F:51])[CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH3:50])=[CH:26][CH:25]=4)=[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 20095042HCID 20095042, compound

Product 1

HCID 20095004HCID 20095004, compoundYield 63.4%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

0.25 g (0.62 mM) of 2-octyl-5-[5-(4-hydroxyphenyl)pyrimidine-2-yl]indan, 0.05 g (0.76 mM) of 85%-potassium hydroxide, 0.23 g (0.76 mM) of 2-fluorooctyl p-toluenesulfonate and 5 ml of n-butanol were placed in a 20 ml-round bottomed flask, followed by heat-refluxing for 7 hours under stirring. After the reaction, the reaction mixture was poured into ice water. The resultant insoluble matter was recovered by filtration and washed with methanol, followed by purification by silica gel column chromatography (eluent: toluene) and recrystallized from a mixture solvent (toluene/methanol) to obtain 0.21 g of 2-octyl-5-[5-{4-(2-fluorooctyloxy)phenyl)pyrimidine-2-yl]indan (Yield: 63.4%). ##STR141##

Workup

  1. temperatureby heat-refluxing for 7 hours
  2. customAfter the reaction
  3. filtrationThe resultant insoluble matter was recovered by filtration
  4. washwashed with methanol
  5. customfollowed by purification by silica gel column chromatography (eluent: toluene)
  6. customrecrystallized from a mixture solvent (toluene/methanol)

Sources & evidence

ORD record
ord-de952f775df34de09f440fbbf4c9fc60
Source dataset
uspto-grants-1995_01
Patent number
US05385692

Reaction notes

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