Benzene → trans 2-(5-Cyano-3,4-dimethoxyphenyl)-4-(3,4,5-trimethoxyphenyl)-1,3-dithiolane

HRID 1684046Notes

Reaction equation

HRID 1684046 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:13]([SH:16])[CH2:14][SH:15])[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10].[C:17]([C:19]1[C:20]([O:29][CH3:30])=[C:21]([O:27][CH3:28])[CH:22]=[C:23]([CH:26]=1)[CH:24]=O)#[N:18].C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.C1C=CC=CC=1>C1C=CC=CC=1.O>[C:17]([C:19]1[C:20]([O:29][CH3:30])=[C:21]([O:27][CH3:28])[CH:22]=[C:23]([C@H:24]2[S:16][C@H:13]([C:5]3[CH:6]=[C:7]([O:11][CH3:12])[C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=3)[CH2:14][S:15]2)[CH:26]=1)#[N:18]

Participants

6

Reactant 4

HCID 241BenzeneHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 190417461-(3,4,5-Trimethoxyphenyl)-1,2-ethanedithiolHCID 190418105-Formyl-2,3-dimethoxybenzonitrile

Product 1

HCID 86750980trans 2-(5-Cyano-3,4-dimethoxyphenyl)-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 (2.36 g, 9.09 mmole), 5-cyano-3,4-dimethoxybenzaldehyde (49) (1.50 g, 7.85 mmole) and 0.788 g of pyridinium para-toluenesulfonate was added to 50 ml dry benzene and refluxed with Dean-Stark removal of the benzene-water azeotrope for 24 hours. The benzene was removed in vacuo, and the remaining oil redissolved in ethyl acetate. The organic layer was washed with 10% NaHCO3 and H2O. The organic layer 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 (2.91 g, 86%).

Workup

  1. customThe benzene was removed in vacuo
  2. dissolutionthe remaining oil redissolved in ethyl acetate
  3. washThe organic layer was washed with 10% NaHCO3 and H2O
  4. dry with materialThe organic layer was 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

Sources & evidence

ORD record
ord-94141a968bb24555b42532c57aedeb4a
Source dataset
uspto-grants-1997_06
Patent number
US05639782

Reaction notes

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