3,4-Dimethoxybenzene-1-thiol → HCID 18790160, compound

HRID 1107161Notes

Reaction equation

HRID 1107161 reaction equation
[Na].[CH3:2][O:3][C:4]1[CH:5]=[C:6]([SH:12])[CH:7]=[CH:8][C:9]=1[O:10][CH3:11].CS(O[CH:18]([CH2:26][CH2:27][CH2:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:19]([CH3:25])([CH3:24])[C:20]([O:22][CH3:23])=[O:21])(=O)=O>CO>[CH3:2][O:3][C:4]1[CH:5]=[C:6]([S:12][CH:18]([CH2:26][CH2:27][CH2:28][CH2:29][C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)[C:19]([CH3:25])([CH3:24])[C:20]([O:22][CH3:23])=[O:21])[CH:7]=[CH:8][C:9]=1[O:10][CH3:11]

Participants

5

Reactant 3

HCID 1365393,4-Dimethoxybenzene-1-thiolHCID 5360545SodiumHCID 18790079HCID 18790079, compound

Product 1

HCID 18790160HCID 18790160, compoundYield 44.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent3×

Procedure

Sodium (0.5 g, 2.2 mmol) is added to MeOH (10 mL) cooled in ice. When the reaction is complete a solution of 3,4-dimethoxybenzenethiol (6 g, 3.5 mmol) in MeOH (5 mL) is added. After 2 minutes a solution of methyl 3-methanesulfonyloxy-2,2-dimethyl-7-phenylheptanoate (3 g, 8.8 mmol) in MeOH (5 mL) is added. The cooling bath is removed and the reaction is stirred at room temperature overnight. The solvent is removed in vacuo, CH2Cl2 (50 mL) added and the solution washed with NaHCO3 (50 mL), 1 N HCl (50 mL) and brine (50 mL). The solution is dried over MgSO4 and the solvent removed in vacuo. The product is purified by column chromatography (silica, 20% ether in petroleum ether) to yield methyl 3-(3,4-dimethoxyphenylsulfanyl)-2,2-dimethyl-7-phenylheptanoate (0.65 g, 18%): 1H NMR (300 MHz, CDCl3) δ 7.29-7.24 (m, 2H), 7.19-7.11 (m, 3H), 7.02-6.91 (m, 2H), 6.77 (d, J=8.2 Hz, 1H), 3,87 (s, 3H), 3.85 (s, 3H), 3.57 (s, 3H), 3.22 (dd, J=10.0, 3.2 Hz, 1H), 2.64-2.51 (m, 3H), 1.81-1.74 (m, 1H), 1.66-1.42 (m, 4H), 1.27 (s, 3H), 1.22 (s, 3H); MS (FAB) m/e 416 (M+).

Workup

  1. temperaturecooled in ice
  2. additionis added
  3. customThe cooling bath is removed
  4. customThe solvent is removed in vacuo, CH2Cl2 (50 mL)
  5. additionadded
  6. washthe solution washed with NaHCO3 (50 mL), 1 N HCl (50 mL) and brine (50 mL)
  7. dry with materialThe solution is dried over MgSO4
  8. customthe solvent removed in vacuo
  9. customThe product is purified by column chromatography (silica, 20% ether in petroleum ether)

Sources & evidence

ORD record
ord-b5d21277a77d480ab156261cc68768c3
Source dataset
uspto-grants-2000_05
Patent number
US06057369

Reaction notes

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