Diethyl Ether → HCID 22005342, compound

HRID 324794Notes

Reaction equation

HRID 324794 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C([O:9][C:10]([C:12]1[C:13]([C:38]2[CH:43]=[CH:42][C:41]([F:44])=[CH:40][CH:39]=2)=[C:14]([CH2:25][O:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[C:30]([C:34]([F:37])([F:36])[F:35])[CH:29]=2)[C:15]([CH:20]2[CH2:24][CH2:23][CH2:22][CH2:21]2)=[N:16][C:17]=1[CH2:18][CH3:19])=O)C.[OH-].[K+].C(OCC)C>O1CCCC1>[CH:20]1([C:15]2[C:14]([CH2:25][O:26][CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[C:30]([C:34]([F:37])([F:35])[F:36])[CH:29]=3)=[C:13]([C:38]3[CH:43]=[CH:42][C:41]([F:44])=[CH:40][CH:39]=3)[C:12]([CH2:10][OH:9])=[C:17]([CH2:18][CH3:19])[N:16]=2)[CH2:24][CH2:23][CH2:22][CH2:21]1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 14797Potassium HydroxideHCID 20647553HCID 20647553, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 22005342HCID 22005342, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A suspension of 30 mg (0.8 mmol) of lithium aluminum hydride in 10 ml of absol. tetrahydrofuran is heated under argon. After this, 212 mg (0.4 mmol) of 2-cyclopentyl-6-ethyl-4-(4-fluorophenyl)-3-(3trifluoromethylbenzyloxymethyl)-pyridine-5-carboxylic acid ethylester dissolved in 10 ml of absolute tetrahydrofuran is added. Next, the mixture is refluxed for 1 h. After cooling to room temperature, 10 ml of a 10% potassium hydroxide solution is added. The resulting sediment is drawn off by suction and boiled off several times with 10 ml of diethyl ether. The combined mother liquors are dried with sodium sulfate, concentrated in a vacuum, and chromatographed over silica gel (mobile solvent ethyl acetate/petroleum ether 2:8).

Workup

  1. additionis added
  2. temperatureNext, the mixture is refluxed for 1 h
  3. dry with materialThe combined mother liquors are dried with sodium sulfate
  4. concentrationconcentrated in a vacuum
  5. customchromatographed over silica gel (mobile solvent ethyl acetate/petroleum ether 2:8)

Sources & evidence

ORD record
ord-2753d3456d094e6eaae8793a7a71121a
Source dataset
uspto-grants-2001_04
Patent number
US06218431B1

Reaction notes

Loading…