Water → HCID 86585675, compound

HRID 1994219Notes

Reaction equation

HRID 1994219 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:20]=[CH:21][C:22]=1[F:23])[C:5]([C:12]1[CH:17]=[CH:16][C:15]([F:18])=[C:14]([F:19])[CH:13]=1)([OH:11])[C:6]([O:8][CH2:9][CH3:10])=[O:7].[C@@:24]12(O)[N:31](C)[C@@H:28]([CH2:29][CH2:30]1)[CH2:27][CH:26]=C2.[Na].O>C(#N)C>[F:1][C:2]1[CH:3]=[C:4]([CH:20]=[CH:21][C:22]=1[F:23])[C:5]([C:12]1[CH:17]=[CH:16][C:15]([F:18])=[C:14]([F:19])[CH:13]=1)([OH:11])[C:6]([O:8][C@@:9]12[N:31]([CH3:24])[C@@H:28]([CH2:29][CH2:30]1)[CH2:27][CH:26]=[CH:10]2)=[O:7]

Participants

6

Reactant 4

HCID 962WaterHCID 5360545Sodium2×HCID 11163248Ethyl 3,3',4,4'-tetrafluorobenzilateHCID 53629842Tropenol

Product 1

HCID 86585675HCID 86585675, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

4.27 g (0.013 mol) of ethyl 3,3′,4,4′-tetrafluorobenzilate 3a, 1.81 g (0.013 mol) of tropenol, and 0.03 g of sodium are heated for 4 hours as a melt at 75 mbar over a bath of boiling water with occasional shaking. After cooling, the sodium residues are dissolved with acetonitrile, the solution is evaporated to dryness and the residue is extracted with dichloromethane/water. The organic phase is washed with water, dried over MgSO4, and evaporated to dryness. The residue remaining is combined with diethylether/petroleum ether (1:9), suction filtered, and washed. Yield: 2.50 g (46% of theory); TLC: Rf value: 0.29 (eluant: sec-butanol/formic acid/water 75:15:10); melting point: 147° C.-148° C.

Workup

  1. temperatureAfter cooling
  2. customthe solution is evaporated to dryness
  3. extractionthe residue is extracted with dichloromethane/water
  4. washThe organic phase is washed with water
  5. dry with materialdried over MgSO4
  6. customevaporated to dryness
  7. filtrationfiltered
  8. washwashed

Sources & evidence

ORD record
ord-cd0ac28d0f1a4be0bc9298f9525f5070
Source dataset
uspto-grants-2010_01
Patent number
US07652138B2

Reaction notes

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