Potassium Carbonate → HCID 86755385, compound

HRID 1107123Notes

Reaction equation

HRID 1107123 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+]>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

5

Reactant 3

HCID 11430Potassium CarbonateHCID 1365393,4-Dimethoxybenzene-1-thiolHCID 86755383HCID 86755383, compound

Product 1

HCID 86755385HCID 86755385, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of methyl (E)-3-chloro-7-phenyl-2-heptenoate (1.3 g, 5.1 mmol), 3,4-dimethoxythiophenol (0.86 g, 5.1 mmol) and potassium carbonate (0.7 g, 5.1 mmol) in methanol (50 mL) is heated under reflux for 3 hours. The mixture is filtered and the filtrate is poured into water 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 (4:1 hexane:ethyl acetate) to obtain methyl (E)-3-[(3,4-dimethoxyphenyl)thio]-7-phenyl-2-heptenoate (0.6 g, 31% ). A small amount is recrystallized from hexane to give m.p. 53-5° C. Anal.(C22H26O4S) C, H: 1H-NMR (300 MHz, CDCl3) δ (TMS) 1.68-1.82 (m, 4H), 2.60-2.70 (m, 2H) 2.80-2.92 (m, 2H), 3.57 (s, 3H), 3.86 (s,3H), 3.90 (s, 3H), 5.12 (s, 1H), 6.82-6.92 (m, 2H), 6.98-7.08 (m, 1H), 7.13-7.31 (m, 5H); MS (EI) m/e 386 (M+).

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 3 hours
  3. filtrationThe mixture is filtered
  4. additionthe filtrate is poured into water
  5. extractionis extracted with ether
  6. washThe organic layer is washed with water
  7. dry with materialis dried over MgSO4
  8. customThe solvent is removed in vacuo
  9. customthe residue is chromatographed (4:1 hexane:ethyl acetate)

Sources & evidence

ORD record
ord-ca1d13c246c34c6696d4994d3ba89027
Source dataset
uspto-grants-2000_05
Patent number
US06057369

Reaction notes

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