Triphenylphosphine → HCID 131728886, compound

HRID 1039489Notes

Reaction equation

[CH:1]1([C:4]2[CH:9]=[CH:8][C:7](/[C:10](/[C:14]3[CH:19]=[CH:18][C:17]([I:20])=[CH:16][CH:15]=3)=[CH:11]/[CH2:12][OH:13])=[CH:6][CH:5]=2)[CH2:3][CH2:2]1.O[C:22]1[CH:33]=[CH:32][C:25]([O:26][CH2:27][C:28]([O:30][CH3:31])=[O:29])=[C:24]([CH3:34])[CH:23]=1.C1(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>[CH:1]1([C:4]2[CH:9]=[CH:8][C:7](/[C:10](/[C:14]3[CH:19]=[CH:18][C:17]([I:20])=[CH:16][CH:15]=3)=[CH:11]/[CH2:12][O:13][C:22]3[CH:33]=[CH:32][C:25]([O:26][CH2:27][C:28]([O:30][CH3:31])=[O:29])=[C:24]([CH3:34])[CH:23]=3)=[CH:6][CH:5]=2)[CH2:3][CH2:2]1

Participants

Conditions

Temperature: 0 °C

Procedure

The above allyl alcohol (0.98 g, 2.60 mmol), methyl (4-hydroxy-2-methylphenoxy)acetate (0.545 g, 2.78 mmol; compound VÚFB-21004) and triphenylphosphine (0.782 g, 2.98 mmol) were dissolved in a mixture of anhydrous toluene (12 mL) and tetrahydrofuran (4 mL). The mixture was cooled to 0° C., kept under nitrogen and a degassed solution of diisopropyl azodicarboxylate (0.587 mL, 2.98 mmol) in anhydrous tetrahydrofuran (5 mL) was added dropwise. The reaction mixture was allowed to warm up to ambient temperature and then was 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 8:1) affording methyl (Z)-[4-[3-(4-cyclopropylphenyl)-3-(4-iodophenyl)allyloxy]-2-methylphenoxy]-acetate as solid mass.

Workup

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

Sources & evidence

ORD record: ord-96cdb3623b7c4c708c19a5389178147d
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08551993B2

Reaction notes

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