Triphenylcarbinol → HCID 54400813, compound

HRID 356851Notes

Reaction equation

HRID 356851 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-d8d9c8611b0a4a60870c170d1debbe8e
Source dataset
uspto-grants-1998_11
Patent number
US05840698

Reaction notes

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