Potassium Carbonate → HCID 18790143, compound

HRID 1107164Notes

Reaction equation

HRID 1107164 reaction equation
CS(O[CH:6]([CH2:14][CH2:15][CH2:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:7]([CH3:13])([CH3:12])[C:8]([O:10][CH3:11])=[O:9])(=O)=O.[CH3:24][O:25][C:26]1[CH:31]=[CH:30][C:29]([SH:32])=[CH:28][CH:27]=1.C(=O)([O-])[O-].[K+].[K+]>CO>[CH3:24][O:25][C:26]1[CH:31]=[CH:30][C:29]([S:32][CH:6]([CH2:14][CH2:15][CH2:16][CH2:17][C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:7]([CH3:12])([CH3:13])[C:8]([O:10][CH3:11])=[O:9])=[CH:28][CH:27]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 127654-MethoxybenzenethiolHCID 18790079HCID 18790079, compound

Product 1

HCID 18790143HCID 18790143, compoundYield 24%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

Methyl 3-methanesulfonyloxy-2,2-dimethyl-7-phenylheptanoate (7.7 g, 23 mmol) and 4-methoxybenzenethiol (5.5 mL, 45 mmol) are dissolved in MeOH (40 mL) and potassium carbonate (4.8 g, 35 mmol) is added and the reaction is heated at 60° C. for 24 hours. The solvent is removed in vacuo and CH2Cl2 (100 mL) added and then washed with NaHCO3 (60 mL), 1 N HCl (60 mL) and brine (100 mL). The solvent is removed in vacuo and the residue purified by column chromatography (silica, 40% petroleum ether in CH2Cl2) to yield methyl 3-(4-methoxyphenylsulfanyl)-2,2-dimethyl-7-phenylheptanoate (2.1 g, 24%). 1H NMR (300 MHz, CDCl3) δ 7.36-7.33 (m, 2H), 7.29-7.12 (m, 5H), 6.82-6.79 (m, 2H), 3.79 (s, 3H), 3.55 (s, 3H), 3.18-3.15 (m, 1H), 2.60-2.53 (m, 2H), 1.85-1.73 (m, 1H), 1.57-1.40 (m, 5H), 1.26 (s, 3H), 1.20 (s, 3H); MS (FAB) m/e 386 (M+).

Workup

  1. customThe solvent is removed in vacuo and CH2Cl2 (100 mL)
  2. additionadded
  3. washwashed with NaHCO3 (60 mL), 1 N HCl (60 mL) and brine (100 mL)
  4. customThe solvent is removed in vacuo
  5. customthe residue purified by column chromatography (silica, 40% petroleum ether in CH2Cl2)

Sources & evidence

ORD record
ord-235a74f727624708a7da7bd16f26f2ca
Source dataset
uspto-grants-2000_05
Patent number
US06057369

Reaction notes

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