Triphenylphosphine → methyl (Z)-[4-[3-(4-iodophenyl)-3-[4-(5-methylthiophen-2-yl)phenyl]allyloxy]-2-methylphenoxy]acetate

HRID 1810633Notes

Reaction equation

[I:1][C:2]1[CH:7]=[CH:6][C:5](/[C:8](/[C:12]2[CH:17]=[CH:16][C:15]([C:18]3[S:19][C:20]([CH3:23])=[CH:21][CH:22]=3)=[CH:14][CH:13]=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:17]=[CH:16][C:15]([C:18]3[S:19][C:20]([CH3:23])=[CH:21][CH:22]=3)=[CH:14][CH:13]=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 (0.65 g, 1.50 mmol), methyl (4-hydroxy-2-methylphenoxy)-acetate (0.33 g, 1.68 mmol; example 2) and triphenylphosphine (0.48 g, 1.83 mmol) were dissolved in a mixture of anhydrous toluene (30 mL) and tetrahydrofuran (10 mL). The mixture was cooled to 0° C., kept under nitrogen and a degassed solution of diisopropyl azodicarboxylate (0.35 mL, 1.77 mmol) in anhydrous tetrahydrofuran (5 mL) was added dropwise during 10 min. The reaction mixture was allowed to warm up the ambient temperature with the bath and then was stirred overnight. The solvents were evaporated in vacuo and the residue was submitted to flash column chromatography (silica gel Fluka 60, hexanes/ethyl acetate 6:1) affording methyl (Z)-[4-[3-(4-iodophenyl)-3-[4-(5-methylthiophen-2-yl)phenyl]-allyloxy]-2-methylphenoxy]acetate as solid mass.

Workup

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

Sources & evidence

ORD record: ord-405ac007da1044f1894679772c8c059f
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08362016B2

Reaction notes

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