Trifluoroacetic acid → Methyl 2-tritylsulfanylacetate

HRID 404202Notes

Reaction equation

HRID 404202 reaction equation
[SH:1][CH2:2][C:3]([O:5][CH3:6])=[O:4].[C:7]1([C:13]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)O)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.FC(F)(F)C(O)=O>C(Cl)(Cl)Cl>[CH3:6][O:5][C:3](=[O:4])[CH2:2][S:1][C:13]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)([C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 6457TriphenylcarbinolHCID 16907Methyl Thioglycolate

Product 1

HCID 262768Methyl 2-tritylsulfanylacetateYield 91.3%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a mixture of methyl mercaptoacetate (5.30 g, 50 mmol) and triphenylmethanol (13.0 g, 50 mmol) in chloroform (20 mL) was added trifloroacetic acid (5 mL) in 5 min. After stirring at room temperature for 1 h, the volatiles were removed in vacuo. The crude product was purified by recrystallization (dichloromethane/Hexane=1/2) to provide Tritylsulfanyl-acetic acid methyl ester (15.9 g, 91%). 1H NMR (300 MHz, CDCl3) δ 7.44-7.38 (m, 6H), 7.34-7.18 (m, 9H), 3.58 (s, 3H), 2.98 (s, 2H).

Workup

  1. customthe volatiles were removed in vacuo
  2. customThe crude product was purified by recrystallization (dichloromethane/Hexane=1/2)

Sources & evidence

ORD record
ord-cf5c44503ef14625aa7cc495c02439ca
Source dataset
uspto-grants-2014_06
Patent number
US08748463B2

Reaction notes

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