Trityl chloride → Methyl 2-tritylsulfanylacetate

HRID 1898952Notes

Reaction equation

HRID 1898952 reaction equation
[C:1](Cl)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:21]([O:25][CH3:26])(=[O:24])[CH2:22][SH:23]>C1(C)C=CC=CC=1>[C:2]1([C:1]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[S:23][CH2:22][C:21]([O:25][CH3:26])=[O:24])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6456Trityl chlorideHCID 16907Methyl Thioglycolate

Product 1

HCID 262768Methyl 2-tritylsulfanylacetateYield 87%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of trityl chloride (Aldrich) (5.0 g, 17.9 mmol) and methyl thioglycolate (2.1 mL, 23.3 mmol) in 50 mL of toluene is heated at reflux overnight. The reaction solution is cooled and concentrated in vacuo. The oily residue is crystallized from ethyl acetate/hexane to give 5.4 g (87%) of methyl [(triphenylmethyl)thio]acetate: melting point 111°-115° C.

Workup

  1. temperatureat reflux overnight
  2. temperatureThe reaction solution is cooled
  3. concentrationconcentrated in vacuo
  4. customThe oily residue is crystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-34f8125248a44acb83a9b3b509b2b007
Source dataset
uspto-grants-1996_11
Patent number
US05571825

Reaction notes

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