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Water → Methyl 2-[(3,4-dimethoxyphenyl)thio]-3-(3-phenylpropyl-1-yl)-1-cyclopentenecarboxylate

HRID 1107128
Notes
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Reaction equation

HRID 1107128 reaction equation
Cl[C:2]1[C:6](=[CH:7][CH2:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:5][CH2:4][C:3]=1[C:16]([O:18][CH3:19])=[O:17].[CH3:20][O:21][C:22]1[CH:23]=[C:24]([SH:30])[CH:25]=[CH:26][C:27]=1[O:28][CH3:29].C(=O)([O-])[O-].[K+].[K+].O>CO>[CH3:20][O:21][C:22]1[CH:23]=[C:24]([S:30][C:2]2[C:6](=[CH:7][CH2:8][CH2:9][C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)[CH2:5][CH2:4][C:3]=2[C:16]([O:18][CH3:19])=[O:17])[CH:25]=[CH:26][C:27]=1[O:28][CH3:29]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 1365393,4-Dimethoxybenzene-1-thiolHCID 69907722Methyl 2-chloro-3-(3-phenylpropyl-1-yl)-1-cyclopentenecarboxylate

Product 1

HCID 69907819Methyl 2-[(3,4-dimethoxyphenyl)thio]-3-(3-phenylpropyl-1-yl)-1-cyclopentenecarboxylateYield 58%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of Methyl 2-chloro-3-(3-phenylpropyl-1-yl)-1-cyclopentenecarboxylate (0.2 g, 0.72 mmol), 3,4-dimethoxythiophenol (0.12 g, 0.72 mmol) and potassium carbonate (0.1 g, 0.72 mmol) in methanol (20 mL) is heated under reflux for 6 hours. After standing at room temperature for 2 days, the mixture is heated under reflux for another 4 hours. The mixture 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 on silica gel (4:1 hexane:ethyl acetate) to provide methyl 2-[(3,4-dimethoxyphenyl)thio]-3-(3-phenylpropyl-1-yl)-1-cyclopentenecarboxylate (0.17 g, 58%): 1H-NMR (300 MHz, CDCl3) δ (TMS) 1.10-1.70 (m, 5H), 1.88-1.98 (m, 1H), 2.31-2.40 (t, 3H), 2.58-2.70 (t, 3H), 3.78 (s, 3H), 3.84 (s, 3H), 3.90 (s, 3H), 6.68-6.75 (d, 1H), 6.95-7.09 (m, 4H), 7.17-7.30 (m, 3H); MS (EI) m/e 412 (M+).

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 6 hours
  3. temperaturethe mixture is heated
  4. temperatureunder reflux for another 4 hours
  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 on silica gel (4:1 hexane:ethyl acetate)

Sources & evidence

ORD record
ord-71ab7b2607e54d7094960a05325e3111
Source dataset
uspto-grants-2000_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06057369

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes