Hydrochloric Acid → HCID 86757160, compound

HRID 1385769Notes

Reaction equation

HRID 1385769 reaction equation
C([O:3][C:4](=[O:22])[CH:5]([CH2:18][CH2:19][O:20][CH3:21])[CH:6]=[CH:7][CH:8]([CH2:14][CH2:15][O:16][CH3:17])[C:9]([O:11]CC)=[O:10])C.[OH-].[Na+].Cl>C1COCC1>[CH3:17][O:16][CH2:15][CH2:14][CH:8]([CH:7]=[CH:6][CH:5]([CH2:18][CH2:19][O:20][CH3:21])[C:4]([OH:22])=[O:3])[C:9]([OH:11])=[O:10]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86757159HCID 86757159, compound

Product 1

HCID 86757160HCID 86757160, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 1.29 g (4.08 mmol) mixture of (E)-(2R,5S)- and -(2RS,5SR)-2,5-bis-(2-methoxy-ethyl)-hex-3-enedioic acid diethyl ester in 10 ml THF was added 33 ml (33 mmol) of 1 M sodium hydroxide solution. After stirring for 18 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 894 mg (84%) of the title compound as a yellow oil. MS m/e (%): 259 ([M−H]−, 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-8b3f1211fac249e0b709bab1035f38f2
Source dataset
uspto-grants-2001_07
Patent number
US06262089B1

Reaction notes

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