Triphenylphosphine → HCID 131728886, compound

HRID 1810665Notes

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-9ac9d4406168445b9fc7a4717fc91a40
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08362016B2

Reaction notes

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