Hydrochloric Acid → HCID 86755386, compound

HRID 1107124Notes

Reaction equation

HRID 1107124 reaction equation
Cl/[C:2](/[CH2:8][CH2:9][CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[CH:3]\[C:4]([O:6][CH3:7])=[O:5].[CH3:18][O:19][C:20]1[CH:21]=[C:22]([SH:28])[CH:23]=[CH:24][C:25]=1[O:26][CH3:27].C(=O)([O-])[O-].[K+].[K+].Cl>CO>[CH3:18][O:19][C:20]1[CH:21]=[C:22]([S:28]/[C:2](/[CH2:8][CH2:9][CH2:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:3]\[C:4]([O:6][CH3:7])=[O:5])[CH:23]=[CH:24][C:25]=1[O:26][CH3:27]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 1365393,4-Dimethoxybenzene-1-thiolHCID 86755384HCID 86755384, compound

Product 1

HCID 86755386HCID 86755386, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of methyl (Z)-3-chloro-7-phenyl-2-heptenoate (0.7 g, 2.77 mmol), 3,4-dimethoxythiophenol (0.47 g, 2.77 mmol) and potassium carbonate (0.38 g, 2.77 mmol) in methanol (30 mL) is heated under reflux for 3 hours. The mixture is added to aqueous HCl and is extracted with ether. The organic layer is washed with water and is dried over MgSO4. The solvent is removed in vacuo and the residue is chromatographed on silica gel (4:1 hexane:ethyl acetate) to produce methyl (Z)-3-[(3,4-dimethoxyphenyl)thio]-7-phenyl-2-heptenoate as an oil (0.8 g, 75% ): 1H-NMR (300 MHz, CDCl3) δ (TMS) 1.30-1.53 (m, 3H), 1.62-1.76 (m, 1H), 2.03-2.18 (m, 2H), 2.38-2.48 (m, 1H), 2.64-2.74 (m, 1H), 3.72 (s, 3H), 3.78-3.90 (m, 6H), 5.78 (s, 1H), 6.72-6.82 (m, 1H), 6.92-7.00 (m, 1H), 7.05-7.10 (m, 1H), 7.20-7.38 (m, 5H).

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 3 hours
  3. extractionis extracted with ether
  4. washThe organic layer is washed with water
  5. dry with materialis dried over MgSO4
  6. customThe solvent is removed in vacuo
  7. customthe residue is chromatographed on silica gel (4:1 hexane:ethyl acetate)

Sources & evidence

ORD record
ord-1063515473834a9abbeb743d25c03047
Source dataset
uspto-grants-2000_05
Patent number
US06057369

Reaction notes

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