Triphenylcarbinol → HCID 54400813, compound

HRID 571016Notes

Reaction equation

HRID 571016 reaction equation
[C:1]([O:5][CH3:6])(=[O:4])[CH2:2][SH:3].[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.CCCCCC>ClC(Cl)Cl>[CH3:6][O:5][C:1](=[O:4])[CH:2]([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)[SH:3]

Participants

5

Reactant 3

HCID 6457TriphenylcarbinolHCID 8058HexaneHCID 16907Methyl Thioglycolate

Product 1

HCID 54400813HCID 54400813, compoundYield 97.5%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

Dissolve 5.0 mL (55.0 mmol) methyl thioglycolate and 14.3 g (55.0 mmol) triphenylmethanol in 80 mL trichloromethane. Then slowly drop 6.9 mL (55.0 mmol) boron trifluoride ethyl ether complex into the solution and stir the solution at room temperature. Use thin layer chromatography (TLC)(chloroform:hexane=1:1) to follow the reaction. After starting material disappeared completely, wash the reaction solution with water (2×100 mL). The organic phase is dried by anhydrous sodium sulfate and then the solvent is removed by vacuum evaporation to get 18.6 g (97.5%) triphenylmethyl thioglycolic acid methyl ester (hereafter referred to as compound 1).

Workup

  1. customthe reaction
  2. washwash the reaction solution with water (2×100 mL)
  3. dry with materialThe organic phase is dried by anhydrous sodium sulfate
  4. customthe solvent is removed by vacuum evaporation

Sources & evidence

ORD record
ord-932a300f7a384c14855dade0f5be6181
Source dataset
uspto-grants-2015_05
Patent number
US09024035B2

Reaction notes

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