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

HRID 1684028Notes

Reaction equation

[H-].[Al+3].[Li+].[H-].[H-].[H-].C(OCC)C.[CH3:12][O:13][C:14]1[CH:15]=[C:16]([CH:26]2[CH2:30][S:29]C(=S)[S:27]2)[CH:17]=[C:18]([O:24][CH3:25])[C:19]=1[O:20][CH2:21][O:22][CH3:23]>C1COCC1>[CH3:12][O:13][C:14]1[CH:15]=[C:16]([CH:26]([SH:27])[CH2:30][SH:29])[CH:17]=[C:18]([O:24][CH3:25])[C:19]=1[O:20][CH2:21][O:22][CH3:23]

Participants

Conditions

Temperature: 0 °C

Procedure

Lithium aluminum hydride (0.622 g, 16.38 mmole) is added to 60 ml dry diethyl ether. To this slurry is added dropwise 4-(3,5-dimethoxy-4-methoxymethoxyphenyl)-1,3-dithiolane-2-thione (33) (3.40 g, 10.24 mmole) predissolved in 35 ml dry THF. The reaction is stirred under an N2 atmosphere until the solution becomes colorless (4 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 (2.47 g, 84%). NMR: (CDCl3) 2.33,d,1H;2.90,m,1H;3.10,m,1H; 3.59,s,3H;3.85,s,6H;4.03,m,1H;5.10,s,2H;6.53,s,2H Melting Point: 84°-85° C. C,H,S analysis: (theoretical, actual) C (49.63,49.52); H (6.25,6.28); S (22.08,22.16).

Workup

custom(4 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 (2.47 g, 84%)

Sources & evidence

ORD record: ord-e1fda570ebe5467995354f390c3047b0
Source dataset: uspto-grants-1997_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05639782

Reaction notes

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