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

HRID 1086466Notes

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.O.C(P(CC)CC)C>CC(C)=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

Conditions

Temperature: -5 °C

Procedure

The title compound of Example 15 (32.2 g, 0.106 mole) and water (1.9 ml) were dissolved in acetone (150 ml) with stirring 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. Analysis Calcd. for C18H14OS (278.31): Calcd.: C, 77.67; H, 5.07; S, 11.52. Found: C, 77.80; H, 5.19; S, 11.68.

Workup

stirringThe reaction was stirred at 0° C. for 1 hour
customThe solvent was evaporated
customthe product isolated by chromatography on silica

Sources & evidence

ORD record: ord-622e19d765fb4909a89c9ca30e8c24b1
Source dataset: uspto-grants-1991_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05030642

Reaction notes

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