Triphenylphosphine → HCID 86629319, compound

HRID 1810683Notes

Reaction equation

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

Participants

Conditions

Temperature: 0 °C

Procedure

The above allyl alcohol (3.40 g, 8.30 mmol), methyl (4-hydroxy-2-methylphenoxy)-acetate (1.79 g, 9.13 mmol; compound VÚFB-21004) and triphenylphosphine (2.5 g, 9.55 mmol) were dissolved in a mixture of anhydrous toluene (38 mL) and tetrahydrofuran (13 mL). The mixture was cooled to 0° C., kept under nitrogen and a degassed solution of diisopropyl azodicarboxylate (1.88 mL, 9.55 mmol) in anhydrous tetrahydrofuran (5 mL) was added dropwise. The reaction mixture was allowed to warm up to ambient temperature 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 10:1-8:1) affording methyl (Z)-[4-[3-(4-cyclopropylsulfanylphenyl)-3-(4-iodophenyl)allyloxy]-2-methyl-phenoxy]acetate as yellowish oil.

Workup

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

Sources & evidence

ORD record: ord-15269197f69c4ce2b7e20fabd454f464
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08362016B2

Reaction notes

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