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

HRID 1074033Notes

Reaction equation

HRID 1074033 reaction equation
[CH2:1]([S:8][C:9]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:10][CH:11]=[C:12](N(C)C)[C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.C([OH:29])C>>[CH2:1]([S:8][C:9]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:10][CH:11]=[C:12]([OH:29])[C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 54057031Diethyl 5-benzylthio-2-dimethylamino-2,4-hexadienedioate

Product 1

HCID 54729633Diethyl 5-benzylthio-2-hydroxy-2,4-hexadienedioate

Conditions

Temperature
20 °C

Procedure

The procedure is as in Example 2, starting with diethyl 5-benzylthio-2-dimethylamino-2,4-hexadienedioate (10 g) and 1N aqueous hydrochloric acid solution (41.3 cc) in ethanol (41.3 cc). The mixture is heated to boiling for 2 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 (30:70 by volume) as eluent, diethyl 5-benzylthio-2-hydroxy-2,4-hexadienedioate (6.3 g) (m.p. <40° C.) is obtained [Rf=0.6; thin layer chromatography on silica gel; eluent: cyclohexane/ethyl acetate (30:70 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 (30:70 by volume) as eluent

Sources & evidence

ORD record
ord-6707be17eb3c42d88954251be668cd5e
Source dataset
uspto-grants-1990_11
Patent number
US04971979

Reaction notes

Loading…