Ethylparaben → 4-[1-(4'-Trifluoromethyl-biphenyl-4-ylmethyl)-propoxy]-benzoic acid methyl ester

HRID 1669290Notes

Reaction equation

HRID 1669290 reaction equation
[F:1][C:2]([F:21])([F:20])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([CH2:15][CH:16]([OH:19])[CH2:17][CH3:18])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.[CH2:22]([O:24][C:25](=[O:33])[C:26]1[CH:31]=[CH:30][C:29](O)=[CH:28][CH:27]=1)C.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O.C(P(CCCC)CCCC)CCC>C1(C)C=CC=CC=1.C(OCC)(=O)C.C(OCC)(=O)C.CCCCCC>[CH3:22][O:24][C:25](=[O:33])[C:26]1[CH:31]=[CH:30][C:29]([O:19][CH:16]([CH2:15][C:12]2[CH:13]=[CH:14][C:9]([C:6]3[CH:5]=[CH:4][C:3]([C:2]([F:20])([F:21])[F:1])=[CH:8][CH:7]=3)=[CH:10][CH:11]=2)[CH2:17][CH3:18])=[CH:28][CH:27]=1

Participants

8

Reactant 4

HCID 8434EthylparabenHCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 673421621-(4'-Trifluoromethyl-biphenyl-4-yl)-butan-2-ol

Product 1

HCID 673425784-[1-(4'-Trifluoromethyl-biphenyl-4-ylmethyl)-propoxy]-benzoic acid methyl esterYield 38%

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

1-(4′-Trifluoromethyl-biphenyl-4-yl)-butan-2-ol (0.088 g, 0.30 mmol) and 4-hydroxy-benzoic acid ethyl ester (0.062 g, 0.37 mmol) are dissolved in toluene (2 mL) under an inert atmosphere of nitrogen. 1,1′-(Azodicarbonyl)dipiperidine (0.114 g, 0.45 mmol) is added, followed by tributyl-phosphane (0.1 mL, 0.45 mmol) at 0° C. The reaction is stirred for eighteen hours at room temperature, diluted with ethyl acetate, filtered and concentrated. Column chromatography on silica gel with 0-40% ethyl acetate/hexane gradient gives 0.050 g (0.11 mmol, 38%) of title compound.

Workup

  1. filtrationfiltered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-ab48e783af654ae78a0d03822b0f96a5
Source dataset
uspto-grants-2011_08
Patent number
US07989457B2

Reaction notes

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