Dicyclohexylcarbodiimide → 4'-Butoxy-2,3,3'-trifluorobiphenyl-4-yl 4'-propylbicyclohexane-4-carboxylate

HRID 2068453Notes

Reaction equation

HRID 2068453 reaction equation
[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[CH:16][C:15]([OH:18])=[C:14]([F:19])[C:13]=2[F:20])=[CH:8][C:7]=1[F:21])[CH2:2][CH2:3][CH3:4].C1(N=C=NC2CCCCC2)CCCCC1.CN(C1C=CC=CN=1)C.[CH2:46]([CH:49]1[CH2:54][CH2:53][CH:52]([CH:55]2[CH2:60][CH2:59][CH:58]([C:61](O)=[O:62])[CH2:57][CH2:56]2)[CH2:51][CH2:50]1)[CH2:47][CH3:48]>C1(C)C=CC=CC=1>[CH2:46]([CH:49]1[CH2:54][CH2:53][CH:52]([CH:55]2[CH2:60][CH2:59][CH:58]([C:61]([O:18][C:15]3[CH:16]=[CH:17][C:12]([C:9]4[CH:10]=[CH:11][C:6]([O:5][CH2:1][CH2:2][CH2:3][CH3:4])=[C:7]([F:21])[CH:8]=4)=[C:13]([F:20])[C:14]=3[F:19])=[O:62])[CH2:57][CH2:56]2)[CH2:51][CH2:50]1)[CH2:47][CH3:48]

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 218852-DimethylaminopyridineHCID 793726trans-4'-Propyl-(1,1'-bicyclohexyl)-4-carboxylic AcidHCID 585007494'-Butoxy-2,3,3'-trifluorobiphenyl-4-ol

Product 1

HCID 585007434'-Butoxy-2,3,3'-trifluorobiphenyl-4-yl 4'-propylbicyclohexane-4-carboxylateYield 67%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

4′-Butoxy-2,3,3′-trifluorobiphenyl-4-ol (T-11) (2.00 g) prepared in Example 8, dicyclohexylcarbodiimide (DCC) (1.46 g) and dimethylaminopyridine (DMAP) (0.08 g) were dissolved in toluene (100 ml), and 4′-propylbicyclohexane-4-carboxylic acid (1.70 g) was added, and then the stirring was continued at room temperature for another 16 hours. After the completion of the reaction, the reaction mixture was filtered and the filtrate was extracted with toluene. The organic layer was washed with a 1N—HCl aqueous solution, a 1N-aqueous sodium hydroxide solution, a saturated aqueous solution of sodium hydrogencarbonate, water and brine, and then dried over anhydrous magnesium sulfate. The solution was concentrated under reduced pressure to leave pale brown solids. Silica gel chromatography (heptane:ethyl acetate=20:1 by volume) and recrystallization (heptane:toluene=4:1 by volume) gave 4′-butoxy-2,3,3′-trifluorobiphenyl-4-yl 4′-propylbicyclohexane-4-carboxylate (1-8-14) as colorless powders (2.39 g) in 67% yield.

Workup

  1. customAfter the completion of the reaction
  2. filtrationthe reaction mixture was filtered
  3. extractionthe filtrate was extracted with toluene
  4. washThe organic layer was washed with a 1N—HCl aqueous solution
  5. dry with materiala 1N-aqueous sodium hydroxide solution, a saturated aqueous solution of sodium hydrogencarbonate, water and brine, and then dried over anhydrous magnesium sulfate
  6. concentrationThe solution was concentrated under reduced pressure
  7. customto leave pale brown solids
  8. customSilica gel chromatography (heptane:ethyl acetate=20:1 by volume) and recrystallization (heptane:toluene=4:1 by volume)

Sources & evidence

ORD record
ord-d59349229b68445e94fdabaf398dabf9
Source dataset
uspto-grants-2012_10
Patent number
US08298632B2

Reaction notes

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