Tetrahydrofuran → HCID 511925, compound

HRID 2290405Notes

Reaction equation

HRID 2290405 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:15])[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:4][CH:3]=1.C1COCC1.CC([O-])(C)C.[K+].C1(CS([C:37]2[CH:42]=[CH:41][C:40]([S:43]([CH2:46][C:47]3[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=3)(=[O:45])=[O:44])=[CH:39][N:38]=2)(=O)=O)C=CC=CC=1>O.C1(C)C=CC=CC=1>[C:9]1([C:8]([C:5]2[CH:4]=[CH:3][C:2]([O:1][C:37]3[CH:42]=[CH:41][C:40]([S:43]([CH2:46][C:47]4[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=4)(=[O:44])=[O:45])=[CH:39][N:38]=3)=[CH:7][CH:6]=2)=[O:15])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 143474-HydroxybenzophenoneHCID 13102686HCID 13102686, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 511925HCID 511925, compoundYield 44%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

To 4.96 g of p-hydroxybenzophenone in a 25 ml THF/25 ml DMSO mixture was added 3.1 g of t-BuOK and then 9.69 g of 2,5bis((phenylmethyl)sulfonyl)pyridine and the resulting mixture heated at 60° C. for 11/2 hrs. The reaction mixture was allowed to cool overnight, diluted with 4 volumes of water, and the golden-brown precipitate which formed removed by filtration. Recrystallization from CH2Cl2 /ethanol and then from toluene gave the product, phenyl(4-((5-((phenylmethyl)sulfonyl)-2-pyridinyl)oxy)phenyl)methanone, (44% yield), as tan prisms, m.p. 146°-147° C.

Workup

  1. temperatureto cool overnight
  2. customthe golden-brown precipitate which formed
  3. customremoved by filtration
  4. customRecrystallization from CH2Cl2 /ethanol

Sources & evidence

ORD record
ord-60e0a81b36f3413cbf4b05688ed44130
Source dataset
uspto-grants-1986_10
Patent number
US04616087

Reaction notes

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