Toluene → HCID 178444463, compound

HRID 1250130Notes

Reaction equation

HRID 1250130 reaction equation
[CH:1]([C@H:3]1[CH2:8][CH2:7][C@H:6]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:5][CH2:4]1)=O.[F:14][C:15]1[CH:16]=[C:17](O)[CH:18]=[CH:19][C:20]=1[O:21][C:22]([F:25])([F:24])[F:23].[CH2:27]1[CH2:32][CH2:31]C(N=C=N[CH:36]2[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37]2)[CH2:29][CH2:28]1.[C:42]1(C)[CH:47]=[CH:46]C=[CH:44][CH:43]=1.Cl[CH2:50]Cl>CN(C1C=CN=CC=1)C>[CH2:29]([C@H:20]1[CH2:19][CH2:18][C@H:17](/[CH:42]=[CH:1]/[C@H:3]2[CH2:4][CH2:5][C@H:6]([C:9]([OH:11])=[O:10])[CH2:7][CH2:8]2)[CH2:16][CH2:15]1)[CH2:28][CH2:27][CH2:32][CH3:31].[CH2:44]([C@H:36]1[CH2:37][CH2:38][C@H:39](/[CH:50]=[CH:1]/[C@H:3]2[CH2:8][CH2:7][C@H:6]([C:9]([O:11][C:12]3[CH:13]=[CH:19][C:20]([O:21][C:22]([F:23])([F:24])[F:25])=[C:15]([F:14])[CH:16]=3)=[O:10])[CH2:5][CH2:4]2)[CH2:40][CH2:41]1)[CH2:43][CH2:42][CH2:47][CH3:46]

Participants

8

Reactant 5

HCID 1140TolueneHCID 6344Dichloromethane2×HCID 10868DicyclohexylcarbodiimideHCID 27833573-Fluoro-4-(trifluoromethoxy)phenolHCID 178472373HCID 178472373, compound

Product 2

HCID 178444463HCID 178444463, compoundHCID 178444464HCID 178444464, compound

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

The (E)-trans-4-(2-(trans-4-pentylcyclohexyl)vinyl)cyclohexanecarboxylic acid, which was prepared by the same manner as in the first step of Example 1 with the exception that ethyl trans-4-formylcyclohexanecarboxylate was used in place of 4-cyanobenzaldehyde, in an amount of 1.1 g (3.6 mmol) was mixed with 0.8 g (3.9 mmol) of 3-fluoro-4-trifluromethoxyphenol, 0.1 g (1.1 mmol) of DMAP, and 20 ml of dichloromethane. To this mixture was added dropwise 4 ml of solution of 1.0 g (4.7 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, 70 ml of toluene was added to the filtrate, and the filtrate was 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-fluoro-4-trifluoromethoxyphenyl trans-4-(2-(trans-4-pentylcyclohexyl)vinyl)cyclohexanecarboxylate. This crude product was recrystallized from a mixed solvent of heptane/diethyl ether to obtain 0.7 g of the subjective compound (yield 38.7%).

Workup

  1. temperaturewhile being cooled with ice in 5 min
  2. customSeparated crystals
  3. filtrationwere filtered off
  4. addition70 ml of toluene was added to the filtrate
  5. washthe filtrate was washed 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-dc8c780d1e0b44b9a4c63627717ed3d8
Source dataset
uspto-grants-2002_01
Patent number
US06337034B1

Reaction notes

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