Triphenylphosphine → methyl (E)-[4-[3-(4-iodophenyl)-3-(3-trifluoromethylphenyl)allyloxy]-2-methylphenoxy]acetate

HRID 1810659Notes

Reaction equation

[I:1][C:2]1[CH:7]=[CH:6][C:5](/[C:8](/[C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[CH:13]=2)=[CH:9]\[CH2:10][OH:11])=[CH:4][CH:3]=1.[CH3:22][C:23]1[CH:33]=[C:32](OC/C=C(/C2C=CC(C#CCN3CCOCC3)=CC=2)\C2C=CC=CC=2)[CH:31]=[CH:30][C:24]=1[O:25][CH2:26][C:27]([OH:29])=[O:28].[C:59]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1(C)C=CC=CC=1.O1CCCC1>[I:1][C:2]1[CH:7]=[CH:6][C:5](/[C:8](/[C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:19])([F:20])[F:21])[CH:13]=2)=[CH:9]\[CH2:10][O:11][C:32]2[CH:31]=[CH:30][C:24]([O:25][CH2:26][C:27]([O:29][CH3:59])=[O:28])=[C:23]([CH3:22])[CH:33]=2)=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 0 °C

Procedure

The above allyl alcohol (2.0 g, 4.94 mmol), methyl (4-hydroxy-2-methylphenoxy)-acetate (1.08 g, 5.54 mmol; example 2) and triphenylphosphine (1.50 g, 6.02 mmol) were dissolved in a mixture of anhydrous toluene (40 mL) and tetrahydrofuran (20 mL). The mixture was cooled to 0° C., kept under argon and a degassed solution of diisopropyl azodicarboxylate (1.15 mL, 5.82 mmol) in anhydrous tetrahydrofuran (10 mL) was added dropwise during 10 min. The reaction mixture was allowed to warm up to ambient temperature with the bath and then was stirred for 20 h. The solvents were evaporated in vacuo and the residue was submitted to flash column chromatography (silica gel Fluka 60, hexanes/ethyl acetate 9:1) affording methyl (E)-[4-[3-(4-iodophenyl)-3-(3-trifluoromethylphenyl)allyloxy]-2-methyl-phenoxy]acetate as yellow oil.

Workup

temperatureto warm up to ambient temperature with the bath
customThe solvents were evaporated in vacuo

Sources & evidence

ORD record: ord-f37146cac3cd4f1d978d13b0e7c75d85
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08362016B2

Reaction notes

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