Hydrochloric Acid → Diethyl 5-allylthio-2-hydroxy-2,4-hexadienedioate

HRID 477315Notes

Reaction equation

HRID 477315 reaction equation
[CH2:1]([S:4][C:5]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:6][CH:7]=[C:8](N(C)C)[C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH:2]=[CH2:3].Cl.C([OH:25])C>>[CH2:1]([S:4][C:5]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:6][CH:7]=[C:8]([OH:25])[C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH:2]=[CH2:3]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 54345555Diethyl 5-allylthio-2-dimethylamino-2,4-hexadienedioate

Product 1

HCID 86743582Diethyl 5-allylthio-2-hydroxy-2,4-hexadienedioate

Conditions

Temperature
20 °C

Procedure

The procedure is as in Example 2, starting with diethyl 5-allylthio-2-dimethylamino-2,4-hexadienedioate (5.1 g) and 1N aqueous hydrochloric acid solution (24.4 cc) in ethanol (24.4 cc). The mixture is heated to boiling for 3 minutes, and then cooled to a temperature in the region of 20° C. After purification by chromatography on a silica column with a mixture of cyclohexane and ethyl acetate (75:25 by volume) as eluent, diethyl 5-allylthio-2-hydroxy-2,4-hexadienedioate (2.3 g) is obtained in the form of a yellow oil [Rf=0.2; thin layer chromatography on silica gel; eluent: cyclohexane/ethyl acetate (75:25 by volume)].

Workup

  1. temperatureThe mixture is heated
  2. customAfter purification by chromatography on a silica column
  3. additionwith a mixture of cyclohexane and ethyl acetate (75:25 by volume) as eluent

Sources & evidence

ORD record
ord-fb2cb413adda4307bc808545c2977640
Source dataset
uspto-grants-1989_12
Patent number
US04886835

Reaction notes

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