Triphenylphosphine → HCID 86629319, compound

HRID 1039507Notes

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-7962203a39714445a6e79b873e9a284b
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08551993B2

Reaction notes

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