Methyl Thioglycolate → HCID 53898036, compound

HRID 1898957Notes

Reaction equation

HRID 1898957 reaction equation
O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH3:13][S:14][C:15]1[CH:28]=[CH:27][C:18]([CH:19](O)[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[CH:17][CH:16]=1.[C:29]([O:33][CH3:34])(=[O:32])[CH2:30][SH:31]>C1(C)C=CC=CC=1.C(OCC)(=O)C>[CH3:13][S:14][C:15]1[CH:28]=[CH:27][C:18]([CH:19]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[S:31][CH2:30][C:29]([O:33][CH3:34])=[O:32])=[CH:17][CH:16]=1

Participants

6

Reactant 3

HCID 16907Methyl ThioglycolateHCID 521998p-Toluenesulfonic acid monohydrateHCID 2760079HCID 2760079, compound

Product 1

HCID 53898036HCID 53898036, compoundYield 56%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of ρ-toluenesulfonic acid monohydrate (50 mg, 0.3 mmol) in 10 mL of toluene, which contains 300-500 mg of activated 3 Å molecular sieves, is added 4-methylthiobenzhydrol (0.30 g, 1.3 mmol) and methyl thioglycolate (140 μL, 1.6 mmol), and the reaction is stirred for 2 hours. The reaction is diluted with ethyl acetate and washed with a saturated solution of sodium bicarbonate, water, followed by brine. The organic phase is dried over magnesium sulfate, filtered, and concentrated in vacuo. The resulting oil is chromatographed on silica gel eluting with ethyl acetate:toluene:hexane (2:18:80) to give 0.23 g (56%) of methyl [[(4-methylthiophenyl)phenylmethyl]thio]acetate as an oil.

Workup

  1. washwashed with a saturated solution of sodium bicarbonate, water
  2. dry with materialThe organic phase is dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe resulting oil is chromatographed on silica gel eluting with ethyl acetate:toluene:hexane (2:18:80)

Sources & evidence

ORD record
ord-cc15a59b3c6e4b79b1be558130f8b413
Source dataset
uspto-grants-1996_11
Patent number
US05571825

Reaction notes

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