Diethyl Ether → 1-(3,4,5-Trimethoxyphenyl)-1,2-ethanedithiol

HRID 1684024Notes

Reaction equation

[H-].[Al+3].[Li+].[H-].[H-].[H-].C(OCC)C.[CH3:12][O:13][C:14]1[CH:15]=[C:16]([CH:24]2[CH2:28][S:27]C(=S)[S:25]2)[CH:17]=[C:18]([O:22][CH3:23])[C:19]=1[O:20][CH3:21]>C1COCC1>[CH3:12][O:13][C:14]1[CH:15]=[C:16]([CH:24]([SH:25])[CH2:28][SH:27])[CH:17]=[C:18]([O:22][CH3:23])[C:19]=1[O:20][CH3:21]

Participants

Conditions

Temperature: 0 °C

Procedure

Lithium aluminum hydride (0.20 g, 5.27 mmole) is added to 15 ml dry diethylether. To this slurry is added 4-(3,4,5-trimethoxyphenyl)-1,3-dithiolane-2-thione (32) (1.0 g, 3.31 mmole) predissolved in 20 ml dry THF. The reaction is refluxed under an N2 atmosphere for 12 hours. The reaction is cooled to 0° C. and the excess hydride destroyed with H2O. The reaction mixture is acidified with 10% HCl and immediately extracted with diethyl ether. The organic layer is washed with H2O, dried over MgSO4, filtered and evaporated to a white solid (9.836 g, 97%). NMR: (DCDl3) 2.34,d,1H;2.95,m,1H;3.09,m,1H; 3.84,s,3H;3.87,s,6H;4.03,m,1H;6.53,s,2H. M.S. (IBu) 261 (100%). Melting Point: 72.5°-73.5° C. C,H,S Analysis: (theoretical, actual) C (50.74,50.85); H (6.19,6.20); S (24.63,24.53).

Workup

temperatureThe reaction is refluxed under an N2 atmosphere for 12 hours
customthe excess hydride destroyed with H2O
extractionimmediately extracted with diethyl ether
washThe organic layer is washed with H2O
dry with materialdried over MgSO4
filtrationfiltered
customevaporated to a white solid (9.836 g, 97%)

Sources & evidence

ORD record: ord-7b315af2b34745e59d8c1f40f6b8183c
Source dataset: uspto-grants-1997_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05639782

Reaction notes

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