Dicyclohexylcarbodiimide → HCID 22852144, compound

HRID 1608891Notes

Reaction equation

HRID 1608891 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[O:11][CH2:12][C@@H:13]([CH3:16])[CH2:14][CH3:15])[C:5]([OH:7])=[O:6].[CH2:17]([C:21]1[CH:26]=[CH:25][C:24]([CH2:27][CH2:28][C:29]2[CH:34]=[CH:33][C:32](O)=[CH:31][CH:30]=2)=[CH:23][CH:22]=1)[CH2:18][CH:19]=[CH2:20].C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C1C=CN=CC=1.CCOCC>[CH2:17]([C:21]1[CH:26]=[CH:25][C:24]([CH2:27][CH2:28][C:29]2[CH:30]=[CH:31][C:32]([O:6][C:5](=[O:7])[C:4]3[CH:8]=[CH:9][C:10]([O:11][CH2:12][C@@H:13]([CH3:16])[CH2:14][CH3:15])=[C:2]([F:1])[CH:3]=3)=[CH:33][CH:34]=2)=[CH:23][CH:22]=1)[CH2:18][CH:19]=[CH2:20]

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 53632934HCID 53632934, compoundHCID 54462859HCID 54462859, compound

Product 1

HCID 22852144HCID 22852144, compoundYield 53.9%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 3283Diethyl EtherSolvent

Procedure

About 4.5 g (0.02 mol) of 3-fluoro-4-[(S)-2-methylbutoxy]benzoic acid (which can be prepared, for example, as described in EP-A 255 962 ), 5.0 g (0.02 mol) of 4-[4-(3-butenyl)phenylethyl]phenol, 4.1 g (0.02 mol) of dicyclohexylcarbodimide and 0.1 g of 4-dimethylaminopyridine were mixed in 40 ml of ether at room temperature. The mixture was first heated to reflux for 4 hours and then stirred at room temperature for 14 hours, and the resulting urea was filtered off. Washing was carried out first with 2N hydrochloric acid and then with NaHCO3 solution, and the ether phase was worked up. Column chromatography on Al2O3 with methyl tert-butyl ether/petroleum ether (1:2) as mobile phase resulted in 4.9 g of [4-[4-(3-butenyl)phenyl]ethylphenyl]-3-fluoro-4-[(S)-2-methylbutoxy]benzoate (yield 53.9%) which showed the following phase behavior: C 77 N* 86 I.

Workup

  1. temperatureThe mixture was first heated
  2. temperatureto reflux for 4 hours
  3. filtrationthe resulting urea was filtered off
  4. washWashing

Sources & evidence

ORD record
ord-3209fee1b16d403fa32b86c183b4d2b8
Source dataset
uspto-grants-1995_03
Patent number
US05399290

Reaction notes

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