Toluene → HCID 178448032, compound

HRID 1250132Notes

Reaction equation

HRID 1250132 reaction equation
[CH2:1]([C@H:6]1[CH2:11][CH2:10][C@H:9]([C@H:12]2[CH2:17][CH2:16][C@H:15](/[CH:18]=[CH:19]/[C:20]3[CH:28]=[CH:27][C:23]([C:24](O)=[O:25])=[CH:22][CH:21]=3)[CH2:14][CH2:13]2)[CH2:8][CH2:7]1)[CH2:2][CH2:3]CC.[F:29][C:30]1[CH:31]=[C:32]([OH:42])[CH:33]=[C:34]([F:41])[C:35]=1[O:36][C:37]([F:40])([F:39])[F:38].C1CCC(N=C=NC2CCCCC2)CC1.C1(C)C=CC=CC=1>CN(C1C=CN=CC=1)C.ClCCl>[CH2:1]([C@H:6]1[CH2:7][CH2:8][C@H:9]([C@H:12]2[CH2:17][CH2:16][C@H:15](/[CH:18]=[CH:19]/[C:20]3[CH:28]=[CH:27][C:23]([C:24]([O:42][C:32]4[CH:31]=[C:30]([F:29])[C:35]([O:36][C:37]([F:39])([F:40])[F:38])=[C:34]([F:41])[CH:33]=4)=[O:25])=[CH:22][CH:21]=3)[CH2:14][CH2:13]2)[CH2:10][CH2:11]1)[CH2:2][CH3:3]

Participants

7

Reactant 4

HCID 1140TolueneHCID 10868DicyclohexylcarbodiimideHCID 178781583,5-Difluoro-4-(trifluoromethoxy)phenolHCID 178444498HCID 178444498, compound

Product 1

HCID 178448032HCID 178448032, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

(E)-4-(2-(trans-4-(trans-4-pentylcyclohexyl)cyclohexyl)vinyl)benzoic acid in an amount of 1,3 g (3.7 mmol), 0.8 g (3.7 mmol) of 3,5-difluoro-4-trifluoromethoxyphenol, 0.1 g (1.1 mmol) of DMAP, and 30 ml of dichloromethane were mixed. To this mixture was added dropwise 5 ml of solution of 1.0 g (4.8 mmol) of DCC in dichloromethane while being cooled with ice in 5 min, and stirred as it was for 12 hours. Separated crystals were filtered off, and 80 ml of toluene was added to the filtrate, washed with 2N-NaOH five times and with water thrice, and then dried over anhydrous magnesium sulfate. The solvent was distilled off under a reduced pressure. The residue thus obtained was subjected to silica gel column chromatography (eluent: toluene) to obtain 1.7 g of a crude (E)-3,5-difluoro-4-trifluoromethoxyphenyl 4-(2-(trans-4-(trans-4-propylcyclohexyl)cyclohexyl)vinyl)benzoate.

Workup

  1. temperaturewhile being cooled with ice in 5 min
  2. customSeparated crystals
  3. filtrationwere filtered off
  4. addition80 ml of toluene was added to the filtrate
  5. washwashed with 2N-NaOH five times and with water thrice
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationThe solvent was distilled off under a reduced pressure
  8. customThe residue thus obtained

Sources & evidence

ORD record
ord-c8ba2a6693dd49ffa4d2b7d1f3c9b450
Source dataset
uspto-grants-2002_01
Patent number
US06337034B1

Reaction notes

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