Triphenylphosphine → 2-Methyl-2-(2-methyl-5-{2-[2-methyl-6-(4-trifluoromethyl-phenyl)-pyridin-3-yl]-ethoxy]-phenoxy)-propionic acid ethyl ester

HRID 1242402Notes

Reaction equation

[CH2:1]([O:3][C:4](=[O:17])[C:5]([O:8][C:9]1[CH:14]=[C:13]([OH:15])[CH:12]=[CH:11][C:10]=1[CH3:16])([CH3:7])[CH3:6])[CH3:2].[CH3:18][C:19]1[C:24]([CH2:25][CH2:26]O)=[CH:23][CH:22]=[C:21]([C:28]2[CH:33]=[CH:32][C:31]([C:34]([F:37])([F:36])[F:35])=[CH:30][CH:29]=2)[N:20]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)(C)C)=O)=NC(OC(C)(C)C)=O>C1COCC1>[CH2:1]([O:3][C:4](=[O:17])[C:5]([CH3:6])([O:8][C:9]1[CH:14]=[C:13]([O:15][CH2:26][CH2:25][C:24]2[C:19]([CH3:18])=[N:20][C:21]([C:28]3[CH:33]=[CH:32][C:31]([C:34]([F:37])([F:35])[F:36])=[CH:30][CH:29]=3)=[CH:22][CH:23]=2)[CH:12]=[CH:11][C:10]=1[CH3:16])[CH3:7])[CH3:2]

Participants

Conditions

Temperature: 0 °C

Procedure

0.24 g (1.0 mmol) of the above prepared 2-(5-hydroxy-2-methyl-phenoxy)-2-methyl-propionic acid ethyl ester, 0.31 g (1.10 mmol) of 2-[2-methyl-6-(4-trifluoromethyl-phenyl)-pyridin-3-yl]-ethanol (see below example 70E]) and 0.32 g (1.20 mmol) of triphenylphosphine were dissolved in 10 ml of THF. The stirred reaction mixture was cooled down to 0° C. and a solution of 0.27 g (1.15 mmol) of di-tert.-butyl azodicarboxylate in 5 ml of THF was added drop by drop. Then, the reaction warmed up to ambient temperature. After 20 hours, the solvent was evaporated and the residue purified by chromatography (SiO2, heptane/EtOAc=95:5 to 9:1) to give 0.23 g of the title compound as colorless oil.

Workup

customThe stirred reaction mixture
temperatureThen, the reaction warmed up to ambient temperature
customthe solvent was evaporated
customthe residue purified by chromatography (SiO2, heptane/EtOAc=95:5 to 9:1)

Sources & evidence

ORD record: ord-cb9457aeb196477f80231c9e155543c0
Source dataset: uspto-grants-2006_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07115611B2

Reaction notes

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