Hydrochloric Acid → HCID 86757157, compound

HRID 1385766Notes

Reaction equation

HRID 1385766 reaction equation
C([O:3][C:4](=[O:22])[CH:5]([CH2:18][CH2:19][CH2:20][CH3:21])[CH:6]=[CH:7][CH:8]([CH2:14][CH2:15][CH2:16][CH3:17])[C:9]([O:11]CC)=[O:10])C.[OH-].[Na+].Cl>C1COCC1>[CH2:18]([CH:5]([CH:6]=[CH:7][CH:8]([CH2:14][CH2:15][CH2:16][CH3:17])[C:9]([OH:11])=[O:10])[C:4]([OH:22])=[O:3])[CH2:19][CH2:20][CH3:21]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86757156HCID 86757156, compound

Product 1

HCID 86757157HCID 86757157, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 435 mg (1.39 mmol) mixture of (E)-(2R,5S)- and -(2RS,5SR)-2,5-dibutyl-hex-3-enedioic acid diethyl ester in 10 ml THF was added 26 ml (26 mmol) of 1 M sodium hydroxide solution. After stirring for 72 h at room temperature, the reaction mixture was acidified to pH 3 by addition of 1 M hydrochloric acid and extracted three times with ethyl acetate. The combined organic phases were washed successively with water and with saturated brine, dried over sodium sulphate, and concentrated in vacuo to afford 346 mg (97%) of the title compound as a white crystalline solid. MS m/e (%): 255 ([M−H]−, 60), 211 ([M−H—CO2]−, 100).

Workup

  1. extractionextracted three times with ethyl acetate
  2. washThe combined organic phases were washed successively with water and with saturated brine
  3. dry with materialdried over sodium sulphate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-cc5118a780fe462bab5138bb9eeb8fd1
Source dataset
uspto-grants-2001_07
Patent number
US06262089B1

Reaction notes

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