Triphenylphosphine → 3-(4-(Trifluromethyl)benzamido)-propyloxyphenyl benzoate

HRID 323689

Reaction equation

HRID 323689 reaction equation
[C:1]([O:9][C:10]1[CH:15]=[C:14](C)[C:13](O)=[C:12](CC)[CH:11]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:20][C:21]([F:36])([F:35])[C:22]1[CH:34]=[CH:33][C:25]([C:26]([NH:28]CCCO)=[O:27])=[CH:24][CH:23]=1.[C:37]1(P(C2C=CC=CC=2)C2C=CC=CC=2)[CH:42]=CC=C[CH:38]=1.N(C(OC(C)C)=O)=NC(OC(C)C)=[O:59]>O1CCCC1>[C:1]([O:9][C:10]1[CH:11]=[CH:12][CH:13]=[C:14]([NH:28][C:26](=[O:27])[C:25]2[CH:33]=[CH:34][C:22]([C:21]([F:35])([F:36])[F:20])=[CH:23][CH:24]=2)[C:15]=1[O:59][CH2:38][CH2:37][CH3:42])(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 220068303-(4-Trifluoromethylbenzamido)propan-1-olHCID 232824092-Ethyl-6-methyl-4-benzoyloxyphenol

Product 1

HCID 1317213683-(4-(Trifluromethyl)benzamido)-propyloxyphenyl benzoateYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a mixture of 0.5 g of crude 3-ethyl-4-hydroxy-5-methylphenyl benzoate, 0.48 g of 3-(4-(trifluoromethyl)benzamido)propan-1-ol, 0.54 g of triphenylphosphine and 10 ml of tetrahydrofuran was added dropwise a solution of 0.41 g of diisopropyl azodicarboxylate dissolved in 2 ml of tetrahydrofuran, while stirring at room temperature. After stirring at room temperature for 24 hours, the reaction mixture was concentrated under reduced pressure to give a residue. The residue was subjected to silica gel chromatography, which afforded 0.87 g of 3-ethyl-5-methyl-4-(3-(4-(trifluromethyl)benzamido)-propyloxyphenyl benzoate (90% yield).

Workup

  1. stirringAfter stirring at room temperature for 24 hours
  2. concentrationthe reaction mixture was concentrated under reduced pressure
  3. customto give a residue

Sources & evidence

ORD record
ord-5a93cc64396e457e8fe9c3cc04a9a64d
Source dataset
uspto-grants-2001_04
Patent number
US06214835B1

Linked notes

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