Benzene → trans-2-(3,5-Dimethoxy-4-methylthiophenyl)-4-(-3,4,5-trimethoxyphenyl)-1,3-dithiolane

HRID 1684042Notes

Reaction equation

HRID 1684042 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:15]([SH:18])[CH2:16][SH:17])[CH:6]=[C:7]([O:13][CH3:14])[C:8]=1[O:9][CH2:10]OC.[CH3:19][O:20][C:21]1[CH:22]=[C:23](C=[C:27]([O:30][CH3:31])[C:28]=1[CH3:29])C=S.C1(C)C=CC([S:38]([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.C1C=CC=CC=1>C1C=CC=CC=1.O>[CH3:19][O:20][C:21]1[C:28]([CH3:29])=[C:27]([O:30][CH3:31])[S:38][C:22]=1[C@H:23]1[S:18][C@H:15]([C:5]2[CH:6]=[C:7]([O:13][CH3:14])[C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=2)[CH2:16][S:17]1

Participants

6

Reactant 4

HCID 241BenzeneHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 190418053,5-Dimethoxy-4-methylthiobenzaldehydeHCID 190418081-(3,5-Dimethoxy-4-methoxymethoxyphenyl)-1,2-ethanedithiol

Product 1

HCID 86750977trans-2-(3,5-Dimethoxy-4-methylthiophenyl)-4-(-3,4,5-trimethoxyphenyl)-1,3-dithiolane

Reagents, catalysts & solvents 1

HCID 22272175Benzene--water (1/1)Solvent

Procedure

1-(3,4,5-trimethoxyphenyl)-1,2-ethanedithiol (39) (0.148 g,0.57 mmole), 3,5-dimethoxy-4-methylthiobenzaldehyde (48) (FIG. 23) (0.11 g, 0.519 mmole) and 0.052 g of pyridinium para-toluenesulfonate was added to 40 ml dry benzene and refluxed with Dean-Stark removal of the benzene- water azeotrope for 48 hours. The benzene was removed in vacuo, and the remaining oil redissolved in dichloromethane. The organic layer was washed with 3×30 ml H2O and was dried over MgSO4, and evaporated in vacuo to an oil which was purified by flash column chromatography with 2:1 hex/ethyl acetate as eluent. The product mixture contains a 1.0/1.0 cis/trans ratio (0.151 g, 64%). The trans isomer was isolated after two recrytallizations of this mixture from methanol.

Workup

  1. customThe benzene was removed in vacuo
  2. dissolutionthe remaining oil redissolved in dichloromethane
  3. washThe organic layer was washed with 3×30 ml H2O
  4. dry with materialwas dried over MgSO4
  5. customevaporated in vacuo to an oil which
  6. customwas purified by flash column chromatography with 2:1 hex/ethyl acetate as eluent
  7. customThe trans isomer was isolated after two recrytallizations of this mixture from methanol

Sources & evidence

ORD record
ord-f30857b31f09454289a06d733e918ece
Source dataset
uspto-grants-1997_06
Patent number
US05639782

Reaction notes

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