Triphenylcarbinol → HCID 54400813, compound

HRID 583643Notes

Reaction equation

HRID 583643 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>C(O)(C(F)(F)F)=O>[C:13]([CH:2]([SH:3])[C:1]([O:5][CH3:6])=[O:4])([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

4

Reactant 2

HCID 6457TriphenylcarbinolHCID 16907Methyl Thioglycolate

Product 1

HCID 54400813HCID 54400813, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

Methyl thioglycolate (0.50 g, 4.71 mmol) was dissolved in 5 mL anhydrous TFA. Triphenylmethanol (1.23 g, 4.71 mmol, 1 equiv.) was added and the deep-red solution was stirred at room temperature for 2 hours. TFA was evaporated and the residue was dissolved in ether (100 mL), washed with saturated sodium bicarbonate (50 mL×2) and brine (50 mL×1), dried over MgSO4, and concentrated to dryness, yielding a white solid (1.64 g, quantitative). Rf =0.45 (20% ether/petroleum ether). Products were confirmed by 1H NMR (400 MHz, CDCl3).

Workup

  1. customTFA was evaporated
  2. dissolutionthe residue was dissolved in ether (100 mL)
  3. washwashed with saturated sodium bicarbonate (50 mL×2) and brine (50 mL×1)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated to dryness
  6. customyielding a white solid (1.64 g, quantitative)

Sources & evidence

ORD record
ord-16b5daa60f67443d8fc20191875e3a70
Source dataset
uspto-grants-1999_07
Patent number
US05929278

Reaction notes

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