Dicyclohexylcarbodiimide → Indane

HRID 1770163Notes

Reaction equation

HRID 1770163 reaction equation
C([CH:9]1[CH2:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14](C3N=CC(O)=CN=3)[CH:15]=2)[CH2:10]1)CCCCCCC.C1CCC(N=C=NC2CCCCC2)CC1>CN(C)C1C=CN=CC=1.C(Cl)Cl>[CH2:17]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH2:10][CH2:9]1

Participants

5

Reactant 2

HCID 10868DicyclohexylcarbodiimideHCID 20095062HCID 20095062, compound

Product 1

HCID 10326IndaneYield 82.7%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

0.2 g (0.60 mM) of 2-octyl-5-(5-hydroxypyrimidine-2-yl)indan, 0.07 g (0.62 mM) of s-(-)-tetrahydro-2-furancarboxylic acid, 0.13 g (0.62 mM) of DCC, 0.01 g of 4-dimethylaminopyridine and 10 ml of methylene chloride were mixed and stirred for 6 hours at room temperature. The resultant N,N'-dichlorhexylurea was recovered by filtration, washed with dichloromethane, and added to the filtrate. The resultant dichloromethane solution was subjected to distillation under reduced pressure. The residue was purified by silica gel column chromatography (eluent: ethyl acetate/methylene chloride=1/10) and recrystallized from a mixture solvent (toluene/ethanol) to obtain 0.15 g of 2-octyl-5-[5-(tetrahydro-2-furancarbonyloxy))pyrimidine-2-yl]indan (Yield: 82.7%). ##STR149##

Workup

  1. filtrationThe resultant N,N'-dichlorhexylurea was recovered by filtration
  2. washwashed with dichloromethane
  3. additionadded to the filtrate
  4. distillationThe resultant dichloromethane solution was subjected to distillation under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (eluent: ethyl acetate/methylene chloride=1/10)
  6. customrecrystallized from a mixture solvent (toluene/ethanol)

Sources & evidence

ORD record
ord-67972578b1da4d1cbd4781f2c889dd91
Source dataset
uspto-grants-1995_01
Patent number
US05385692

Reaction notes

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