4-Hydroxybiphenyl → HCID 18646669, compound

HRID 2249138Notes

Reaction equation

HRID 2249138 reaction equation
[H-].[Na+].[C:3]1([C:9]2[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.S([O:26][C@@H:27]([CH2:29][C@H:30](O)[CH3:31])[CH3:28])(C1C=CC(C)=CC=1)(=O)=O>CN(C=O)C>[C:3]1([C:9]2[CH:10]=[CH:11][C:12]([O:15][C@H:30]([CH2:29][C@@H:27]([OH:26])[CH3:28])[CH3:31])=[CH:13][CH:14]=2)[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 71034-HydroxybiphenylHCID 24758Sodium hydrideHCID 53902511HCID 53902511, compound

Product 1

HCID 18646669HCID 18646669, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

0.26 g of 55% sodium hydride was mixed with 5 ml of DMF and 0.85 g of 4-phenylphenol was added dropwise thereto. After the completion of the reaction, 1.42 g of optically active (R,R)-2,4-pentanediol monotosylate in 5 ml of DMF was added dropwise thereto. After reacting at 90° C. for three hours, the reaction mixture was treated in a conventional manner. Then it was purified by silica gel column chromatography with the use of a mixture of n-hexane with ethyl acetate (7/3) as a developing solvent. Thus 0.77 g of optically active (S,S)-2-(4'-phenylphenoxy)pentan-4-ol was obtained. Separately, 0.08 g of 55% sodium hydride was mixed with 3 ml of DMF and a solution of 0.49 g of 5-n-decylpyrimidine in 3 of DMF was added dropwise thereto. Then a solution of 0.71 g of the (S,S)-2-(4'-phenylphenoxy)pentane-4-ol tosylate obtained above in 3 ml of DMF was added dropwise thereto and the obtained mixture was stirred at 90° C. for five hours. After cooling, the reaction mixture was poured into 100 ml of ice/water, extracted with ethyl ether, dried and freed of the solvent. The residue was then purified by silica gel column chromatography with the use of a mixture of n-hexane with ethyl acetate (8/2) as a developing solvent. Thus 0.82 g of optically active (s,S)-2-(4'-phenylphenoxy)-4-[4'-(5"-dicylpyrimidin-2"-yl)phenoxy]pentane was obtained.

Workup

  1. additionwas added dropwise
  2. additionwas added dropwise
  3. additionthe reaction mixture was treated in a conventional manner
  4. customThen it was purified by silica gel column chromatography with the use of a mixture of n-hexane with ethyl acetate (7/3) as a developing solvent

Sources & evidence

ORD record
ord-2ef5702ae683423a944a2ced81548763
Source dataset
uspto-grants-1991_08
Patent number
US05043094

Reaction notes

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