Ethanol → Ethyl 5-propyl-2-(3',4',5'-trifluoro-3-hydroxybiphenyl-4-yl)cyclohexanecarboxylate

HRID 1672103Notes

Reaction equation

HRID 1672103 reaction equation
[CH2:1]([CH:4]1[CH2:27][C:8]2[C:9](=[O:26])[O:10][C:11]3[C:16]([C:7]=2[CH2:6][CH2:5]1)=[CH:15][CH:14]=[C:13]([C:17]1[CH:22]=[C:21]([F:23])[C:20]([F:24])=[C:19]([F:25])[CH:18]=1)[CH:12]=3)[CH2:2][CH3:3].[CH2:28](O)[CH3:29].[O-:31]CC.[Na+].O>C1COCC1.[Pd]>[CH2:1]([CH:4]1[CH2:27][CH:8]([C:9]([O:10][CH2:28][CH3:29])=[O:26])[CH:7]([C:16]2[CH:15]=[CH:14][C:13]([C:17]3[CH:22]=[C:21]([F:23])[C:20]([F:24])=[C:19]([F:25])[CH:18]=3)=[CH:12][C:11]=2[OH:31])[CH2:6][CH2:5]1)[CH2:2][CH3:3]

Participants

7

Reactant 4

HCID 702EthanolHCID 962WaterHCID 2723922Sodium ethoxideHCID 166567888-Propyl-3-(3,4,5-trifluorophenyl)-7,8,9,10-tetrahydrobenzo[c]chromen-6-one

Product 1

HCID 67351318Ethyl 5-propyl-2-(3',4',5'-trifluoro-3-hydroxybiphenyl-4-yl)cyclohexanecarboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

10 g (26.9 mmol) of 8-propyl-3-(3,4,5-trifluorophenyl)-7,8,9,10-tetrahydrobenzo[c]chromen-6-one from Example 1 (1.2.) are dissolved in THF and hydrogenated to cessation in the presence of palladium/active carbon catalyst. The mixture is subsequently filtered, the solvent is removed under reduced pressure, and the residue is dissolved in abs. ethanol and, after addition of 5.5 g (80.7 mmol) of sodium ethoxide, refluxed overnight. After addition of water, the mixture is acidified, the solution is extracted with MTB ether and dried over sodium sulfate. The solvent is removed under reduced pressure, and the crude product is purified by crystallisation, giving ethyl 5-propyl-2-(3′,4′,5′-trifluoro-3-hydroxybiphenyl-4-yl)cyclohexanecarboxylate.

Workup

  1. filtrationThe mixture is subsequently filtered
  2. customthe solvent is removed under reduced pressure
  3. dissolutionthe residue is dissolved in abs
  4. temperaturerefluxed overnight
  5. extractionthe solution is extracted with MTB ether
  6. dry with materialdried over sodium sulfate
  7. customThe solvent is removed under reduced pressure
  8. customthe crude product is purified by crystallisation

Sources & evidence

ORD record
ord-2785fe46b87744e1b53f4fac9cc01ac2
Source dataset
uspto-grants-2011_08
Patent number
US07998541B2

Reaction notes

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