Triphenylphosphine → methyl (Z)-[4-[3-(4-tert-butylphenyl)-3-(4-iodophenyl)allyloxy]-2-methylphenoxy]acetate

HRID 1039475Notes

Reaction equation

[C:1]([C:5]1[CH:10]=[CH:9][C:8](/[C:11](/[C:15]2[CH:20]=[CH:19][C:18]([I:21])=[CH:17][CH:16]=2)=[CH:12]/[CH2:13][OH:14])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[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>[C:1]([C:5]1[CH:10]=[CH:9][C:8](/[C:11](/[C:15]2[CH:20]=[CH:19][C:18]([I:21])=[CH:17][CH:16]=2)=[CH:12]/[CH2:13][O:14][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:7][CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 0 °C

Procedure

The above allyl alcohol (2.46 g, 6.27 mmol), methyl (4-hydroxy-2-methylphenoxy)acetate (1.35 g, 6.88 mmol; example 2) and triphenylphosphine (1.97 g, 7.51 mmol) were dissolved in a mixture of anhydrous toluene (135 mL) and tetrahydrofuran (45 mL). The mixture was cooled to 0° C., kept under nitrogen and a degassed solution of diisopropyl azodicarboxylate (1.5 mL, 7.57 mmol) in anhydrous tetrahydrofuran (15 mL) was added dropwise during 30 min. The reaction mixture was allowed to warm up the ambient temperature with the bath and then stirred over night. The solvents were evaporated in vacuo and the residue was submitted to flash column chromatography (silica gel Fluka 60, hexanes/ethyl acetate 12:1-10:1) affording methyl (Z)-[4-[3-(4-tert-butylphenyl)-3-(4-iodophenyl)allyloxy]-2-methylphenoxy]acetate as yellow oil.

Workup

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

Sources & evidence

ORD record: ord-91670d7c60bc4a1c9348d219ba73ed0f
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08551993B2

Reaction notes

Loading…