Triphenylphosphine → HCID 117966963, compound

HRID 522454Notes

Reaction equation

HRID 522454 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([S:9]([CH2:11][C:12]([F:15])([F:14])[F:13])=[O:10])=[CH:4][C:3]=1[OH:16].[F:17][C:18]([F:30])([F:29])[O:19][C:20]1[CH:25]=[CH:24][C:23]([CH2:26][CH2:27]O)=[CH:22][CH:21]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>O1CCCC1>[F:17][C:18]([F:29])([F:30])[O:19][C:20]1[CH:21]=[CH:22][C:23]([CH2:26][CH2:27][O:16][C:3]2[CH:4]=[C:5]([S:9]([CH2:11][C:12]([F:14])([F:15])[F:13])=[O:10])[C:6]([CH3:8])=[CH:7][C:2]=2[CH3:1])=[CH:24][CH:25]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 107507662-[4-(Trifluoromethoxy)phenyl]ethanolHCID 117899631HCID 117899631, compound

Product 1

HCID 117966963HCID 117966963, compoundYield 40.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In 30 ml of tetrahydrofuran were dissolved 0.3 g (1.19 mmol) of 2,4-dimethyl-5-(2,2,2-trifluoroethylsulfinyl)phenol, 0.29 g (1.41 mmol) of 2-(4′-trifluoromethoxyphenyl)ethanol and 0.41 g (1.56 mmol) of triphenylphosphine. Thereto was added 0.31 g (1.53 mmol) of diisopropyl azodicarboxylate at room temperature, and stirred for 16 hours. The solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (developing solvent: a mixed solvent of n-hexane:ethyl acetate=5:1), and the residue was washed with n-hexane, to obtain 0.21 g (yield: 40%) of an intended product.

Workup

  1. distillationThe solvent was distilled off under reduced pressure
  2. customThe residue was purified by silica gel column chromatography (
  3. washa mixed solvent of n-hexane:ethyl acetate=5:1), and the residue was washed with n-hexane

Sources & evidence

ORD record
ord-4465b8af0b494552a868cd7d1b492ab5
Source dataset
uspto-grants-2016_05
Patent number
US09332754B2

Reaction notes

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