Tributylvinyltin → HCID 10311395, compound

HRID 1985269Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:36])[C:4]([O:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][CH2:16][CH:17]2[CH2:21][N:20]([CH2:22][C:23]3[CH:28]=[CH:27][C:26]([C:29]([CH3:32])([CH3:31])[CH3:30])=[CH:25][CH:24]=3)[C:19](=[O:33])[N:18]2[CH3:34])=[CH:10][C:9]=1I)([CH3:6])[CH3:5].[CH2:37]([Sn](CCCC)(CCCC)C=C)[CH2:38]CC>C1(C)C=CC=CC=1.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:1][O:2][C:3](=[O:36])[C:4]([O:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][CH2:16][CH:17]2[CH2:21][N:20]([CH2:22][C:23]3[CH:28]=[CH:27][C:26]([C:29]([CH3:32])([CH3:31])[CH3:30])=[CH:25][CH:24]=3)[C:19](=[O:33])[N:18]2[CH3:34])=[CH:10][C:9]=1[CH:37]=[CH2:38])([CH3:6])[CH3:5]

Participants

Conditions

Temperature: 80 °C

Procedure

2-(4-{3-[1-(4-tert-Butyl-benzyl)-3-methyl-2-oxo-imidazolidin-4-yl]-propyl}-2-iodo-phenoxy)-2-methyl-propionic acid methyl ester (0.264 g, 0.435 mmole) and tributyl(vinyl) tin (0.207 g, 0.652 mmole) were mixed in toluene (4.0 mL). After bubbled with nitrogen for 15 minutes, tetrakis(triphenylphosphine) palladium(0) (0.050 g, 0.043 mmole) was added. The reaction was heated at 80° C. overnight. The solvent was removed on rota-vapor, and the crude product was purified by column chromatography (silica gel, gradient elution 0-30% acetone in hexane) to provide a colorless oil (0.158 g, 71%). Mass [EI+] 507 (M+H)+.

Workup

customAfter bubbled with nitrogen for 15 minutes
customThe solvent was removed on rota-vapor
customthe crude product was purified by column chromatography (silica gel, gradient elution 0-30% acetone in hexane)

Sources & evidence

ORD record: ord-e706955b162c4ec284b87fa4361f4dee
Source dataset: uspto-grants-2009_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07544812B2

Reaction notes

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