Triphenylphosphine → ethyl 4-(1-(2-methyl-4-(4-(trifluoromethyl)-1H-pyrazol-1-yl)phenoxy)butyl)benzoate

HRID 1520941Notes

Reaction equation

HRID 1520941 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([N:8]2[CH:12]=[C:11]([C:13]([F:16])([F:15])[F:14])[CH:10]=[N:9]2)[CH:5]=[CH:4][C:3]=1[OH:17].O[CH:19]([C:23]1[CH:33]=[CH:32][C:26]([C:27]([O:29][CH2:30][CH3:31])=[O:28])=[CH:25][CH:24]=1)[CH2:20][CH2:21][CH3:22].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC=[N+]=[N-])=O)=NC([O-])=O>O1CCCC1>[CH3:1][C:2]1[CH:7]=[C:6]([N:8]2[CH:12]=[C:11]([C:13]([F:16])([F:15])[F:14])[CH:10]=[N:9]2)[CH:5]=[CH:4][C:3]=1[O:17][CH:19]([C:23]1[CH:33]=[CH:32][C:26]([C:27]([O:29][CH2:30][CH3:31])=[O:28])=[CH:25][CH:24]=1)[CH2:20][CH2:21][CH3:22]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 67981039Ethyl 4-(1-hydroxybutyl)benzoate2×HCID 681562662-methyl-4-(4-(trifluoromethyl)-1H-pyrazol-1-yl)phenolHCID 86669091Diazoethyl azodicarboxylate

Product 1

HCID 68157265ethyl 4-(1-(2-methyl-4-(4-(trifluoromethyl)-1H-pyrazol-1-yl)phenoxy)butyl)benzoateYield 24.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-Methyl-4-(4-(trifluoromethyl)-1H-pyrazol-1-yl)phenol (200 mg, 0.83 mmol) was combined with ethyl 4-(1-hydroxybutyl)benzoate (see Intermediate 5) (19 mg, 0.87 mmol) and dissolved in anhydrous tetrahydrofuran (5 mL). Triphenylphosphine (347 mg, 1.3 mmol) was added at 0° under stirring followed by 0.83 ml of 1.5 M solution of diazoethyl azodicarboxylate (1.24 mmol). The reaction was stirred at room temperature as a yellow solution. At 17 hours, the reaction was concentrated and 10 ml of ethyl acetate and 5 ml of heptanes were added. Solid was filtered off and the mother liquor was loaded on silica gel. Chromatography on a silica gel column (gradient from 5% to 40% of ethyl acetate in heptane) gave the target product as a colorless glass (90 mg, 24%). MS (M+1): 447.2.

Workup

  1. stirringThe reaction was stirred at room temperature as a yellow solution
  2. concentrationthe reaction was concentrated
  3. addition10 ml of ethyl acetate and 5 ml of heptanes were added
  4. filtrationSolid was filtered off

Sources & evidence

ORD record
ord-a8876be91562464492c335ea2d9b5337
Source dataset
uspto-grants-2015_07
Patent number
US09073871B2

Reaction notes

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