Triethylphosphine → 5'-Mercapto[1,1':3',1"-terphenyl]-2'-ol

HRID 703100Notes

Reaction equation

HRID 703100 reaction equation
[OH:1][C:2]1[C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:6][C:5]([S:14]C#N)=[CH:4][C:3]=1[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(P(CC)CC)C>CC(C)=O.O>[SH:14][C:5]1[CH:4]=[C:3]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:2]([OH:1])=[C:7]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:6]=1

Participants

5

Reactant 2

HCID 27365TriethylphosphineHCID 138229422'-Hydroxy[1,1':3',1"-terphenyl]5'-yl thiocyanate

Product 1

HCID 149891685'-Mercapto[1,1':3',1"-terphenyl]-2'-ol

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Conditions

Temperature
-5 °C

Procedure

2'-Hydroxy[1,1':3',1"-terphenyl]-5'-yl thiocyanate (32.2 g, 0.106 mole) was dissolved in acetone (150 ml) and water (1.9 ml), stirred and cooled to -5° C. Triethylphosphine (15.7 ml, 0.106 mole) was added dropwise over a period of 40 minutes. The reaction was stirred at 0° C. for 1 hour and then at room temperature for 2 hours. The solvent was evaporated and the product isolated by chromatography on silica.

Workup

  1. waitat room temperature for 2 hours
  2. customThe solvent was evaporated
  3. customthe product isolated by chromatography on silica

Sources & evidence

ORD record
ord-1fb30d3c29104ab5941db7f7a09e6676
Source dataset
uspto-grants-1991_01
Patent number
US04981853

Reaction notes

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