HCID 18961527, compound → HCID 18961521, compound

HRID 1707541Notes

Reaction equation

HRID 1707541 reaction equation
[CH2:1]([C:11]1[CH:12]=[N:13][C:14]([C:17]2[CH:33]=[CH:32][C:20]([CH2:21][CH:22]([CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])[C:23]([OH:25])=O)=[CH:19][CH:18]=2)=[N:15][CH:16]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]>O>[CH2:26]([CH:22]1[CH2:21][C:20]2[C:32](=[CH:33][C:17]([C:14]3[N:15]=[CH:16][C:11]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10])=[CH:12][N:13]=3)=[CH:18][CH:19]=2)[C:23]1=[O:25])[CH2:27][CH2:28][CH2:29][CH2:30][CH3:31]

Participants

3

Reactant 1

HCID 18961527HCID 18961527, compound

Product 1

HCID 18961521HCID 18961521, compoundYield 65.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
130 °C

Procedure

0.4 g (0.88 mM) of 2-[4-(5-decylpyrimidine-2-yl)benzyl]octanoic acid and 1.3 g of polyphosphoric acid were placed in a flask, followed by stirring for 6 hours at 130° C. After the reaction, 10 ml of water was added to the reaction mixture, followed by extraction with toluene. The extract was dried, followed by distilling-off of the solvent to obtain a crude product. The crude product was purified by silica gel column chromatography (eluent: toluene/ethyl acetate=100/1) and recrystallized from a mixture solvent (toluene/methanol) to obtain 0.25 g (0.57 mM) of 2-hexyl-6-(5-decylpyrimidine-2-yl)-1-indanone (Yield: 65%, m.p.=87° C.).

Workup

  1. additionwas added to the reaction mixture
  2. extractionfollowed by extraction with toluene
  3. customThe extract was dried
  4. customto obtain a crude product
  5. customThe crude product was purified by silica gel column chromatography (eluent: toluene/ethyl acetate=100/1)
  6. customrecrystallized from a mixture solvent (toluene/methanol)

Sources & evidence

ORD record
ord-7503ffd96da64b71b3203a26d4866226
Source dataset
uspto-grants-1994_10
Patent number
US05354501

Reaction notes

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