Triphenylphosphine → Methyl (e)-[4-[3-(4-iodophenyl)-3-(6-phenylpyridin-3-yl)allyloxy]-2-methylphenoxy]acetate

HRID 1810655Notes

Reaction equation

[I:1][C:2]1[CH:7]=[CH:6][C:5](/[C:8](/[C:12]2[CH:13]=[N:14][C:15]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[CH:16][CH:17]=2)=[CH:9]\[CH2:10][OH:11])=[CH:4][CH:3]=1.[CH3:24][C:25]1[CH:35]=[C:34](OC/C=C(/C2C=CC(C#CCN3CCOCC3)=CC=2)\C2C=CC=CC=2)[CH:33]=[CH:32][C:26]=1[O:27][CH2:28][C:29]([OH:31])=[O:30].[C:61]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:13]=[N:14][C:15]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[CH:16][CH:17]=2)=[CH:9]\[CH2:10][O:11][C:34]2[CH:33]=[CH:32][C:26]([O:27][CH2:28][C:29]([O:31][CH3:61])=[O:30])=[C:25]([CH3:24])[CH:35]=2)=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 0 °C

Procedure

The above allyl alcohol (238 mg, 0.0.65 mmol), methyl (4-hydroxy-2-methyl-phenoxy)acetate (140 mg, 0.715 mmol; example 2) and triphenylphosphine (205 mg, 0.78 mmol) were dissolved in a mixture of anhydrous toluene (8 mL) and tetrahydrofuran (6 mL). The mixture was cooled to 0° C., kept under argon and a degassed solution of diisopropyl azodicarboxylate (0.163 mL, 0.78 mmol) in anhydrous tetrahydrofuran (1 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 3 days. The solvents were evaporated in vacuo and the residue was submitted to flash column chromatography (silica gel Fluka 60, hexanes/ethyl acetate 85:15) affording methyl (E)-[4-[3-(4-iodophenyl)-3-(6-phenylpyridin-3-yl)allyloxy]-2-methylphenoxy]acetate as oil.

Workup

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

Sources & evidence

ORD record: ord-64535e44ffa44c18b0d7a26d3b0b0c06
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08362016B2

Reaction notes

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