Dimethylformamide → trans-1,2-Bis(6-decyl-3-methylthionaphthalen-2-yl)ethylene

HRID 1476374Notes

Reaction equation

CN(C=O)C.[CH2:6]([C:16]1[CH:17]=[C:18]2[C:23](=[CH:24][CH:25]=1)[CH:22]=[C:21](OS(C(F)(F)F)(=O)=O)[C:20]([S:34][CH3:35])=[CH:19]2)[CH2:7][CH2:8][CH2:9][CH2:10]CCCCC>O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:25]([C:24]1[CH:23]=[C:22]2[C:6](=[CH:7][CH:8]=1)[CH:16]=[C:19](/[CH:18]=[CH:17]/[C:21]1[C:20]([S:34][CH3:35])=[CH:19][C:18]3[C:23](=[CH:24][CH:25]=[C:16]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[CH:17]=3)[CH:22]=1)[C:20]([S:34][CH3:35])=[CH:21]2)[CH2:16][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:24][CH2:23][CH3:22]

Participants

Conditions

Temperature: 90 °C

Procedure

Pd(PPh3)4 (322 mg, 0.29 mmol, 7 mol %) was added to a DMF (40 ml) solution of 6-decyl-3-methylthio-2-(trifluoromethanesulfonyloxy)naphthalene (compound (4)-81) (1.9 g, 4.1 mmol) and 1,2-bis(tributylstanyl)ethylene (compound (5)-05). The mixture was heated and stirred at 90° C. for 17 hours in a dark place, diluted with water, and extracted with chloroform. The extracted solution was dried with MgSO4, and condensed. The residue was refined by column chromatography (silica gel, developed with dichloromethane) to obtain trans-1,2-bis(6-decyl-3-methylthionaphthalen-2-yl)ethylene (compound (6)-64) (2.3 g, quantitative) as a yellow solid.

Workup

temperatureThe mixture was heated
extractionextracted with chloroform
dry with materialThe extracted solution was dried with MgSO4, and condensed

Sources & evidence

ORD record: ord-b461464825884dc88a49c9c2d00db565
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09018630B2

Reaction notes

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