4-Fluorophenol → HCID 66626126, compound

HRID 2167244Notes

Reaction equation

HRID 2167244 reaction equation
[C:1]([N:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C@@H:7]([OH:14])[CH2:6][C@@H:5]1[CH3:15])(=[O:3])[CH3:2].[F:16][C:17]1[CH:22]=[CH:21][C:20](O)=[CH:19][CH:18]=1.C(P(CCCC)CCCC)CCC>C1(C)C=CC=CC=1>[C:1]([N:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C@H:7]([O:14][C:20]2[CH:21]=[CH:22][C:17]([F:16])=[CH:18][CH:19]=2)[CH2:6][C@@H:5]1[CH3:15])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 97324-FluorophenolHCID 13831TributylphosphineHCID 66626005HCID 66626005, compound

Product 1

HCID 66626126HCID 66626126, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
50 °C

Procedure

50 mg of trans-1-acetyl-4-hydroxy-2-methyl-1,2,3,4-tetrahydroquinoline, 112 mg of 4-fluorophenol, 126 mg of 1,1-azodicarbonyldipiperidine, and 125 mg of tributylphosphine were dissolved in 2 mL of toluene, and the solution was stirred for 2 hours at 50° C. The reaction liquid was filtered to remove any insoluble materials, and then the filtrate was concentrated under reduced pressure. The resulting residue was purified by using silica gel chromatography (diethyl ether), and thus 26 mg (yield 36%) of the title compound was obtained as a colorless oily substance.

Workup

  1. customThe reaction liquid
  2. filtrationwas filtered
  3. customto remove any insoluble materials
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe resulting residue was purified

Sources & evidence

ORD record
ord-919e05b5465449c8a01e15ce831914ba
Source dataset
uspto-grants-2015_06
Patent number
US09045423B2

Reaction notes

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