Benzene → trans-2-(3-(2-Hydroxyethylsufonyl)-5-methoxy-4-propoxyphenyl)-4-(3,4,5-trimethoxyphenyl)-1,3-dithiolane

HRID 1684047Notes

Reaction equation

HRID 1684047 reaction equation
[OH:1][CH2:2][CH2:3][S:4]([C:7]1[CH:8]=[C:9]([CH:12]=[C:13]([O:19][CH3:20])[C:14]=1[O:15][CH2:16][CH2:17][CH3:18])[CH:10]=O)(=[O:6])=[O:5].[CH3:21][O:22][C:23]1[CH:24]=[C:25]([CH:35]([SH:38])[CH2:36][SH:37])[CH:26]=[C:27]([O:33][CH3:34])[C:28]=1[O:29][CH2:30]OC.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.C1C=CC=CC=1>C1C=CC=CC=1.O>[OH:1][CH2:2][CH2:3][S:4]([C:7]1[CH:8]=[C:9]([C@H:10]2[S:38][C@H:35]([C:25]3[CH:24]=[C:23]([O:22][CH3:21])[C:28]([O:29][CH3:30])=[C:27]([O:33][CH3:34])[CH:26]=3)[CH2:36][S:37]2)[CH:12]=[C:13]([O:19][CH3:20])[C:14]=1[O:15][CH2:16][CH2:17][CH3:18])(=[O:6])=[O:5]

Participants

6

Reactant 4

HCID 241BenzeneHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 190417623-(2-Hydroxyethylsulfonyl)-5-methoxy-4-propoxybenzaldehydeHCID 190418081-(3,5-Dimethoxy-4-methoxymethoxyphenyl)-1,2-ethanedithiol

Product 1

HCID 86750981trans-2-(3-(2-Hydroxyethylsufonyl)-5-methoxy-4-propoxyphenyl)-4-(3,4,5-trimethoxyphenyl)-1,3-dithiolane

Reagents, catalysts & solvents 1

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

Procedure

1-(3-(2-hydroxyethylsulfonyl)-5-methoxy-4-propoxybenzaldehyde (54) (FIG. 24) (0.88 g,2.91 mmole), 1-(3,4,5-trimethoxyphenyl)-1,2-ethanedithiol (39) (FIG. 19) (0.947 g, 3.64 mmole) and 0.365 g of pyridinium para-toluene sulfonate was added to 120 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 dichloromethane. 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 1:1 hex/ethyl acetate as eluent. The product mixture (white foam) contains a 1.0/1.0 cis/trans ratio (1.254 g, 79%).

Workup

  1. customThe benzene was removed in vacuo
  2. dissolutionthe remaining oil redissolved in dichloromethane
  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 1:1 hex/ethyl acetate as eluent

Sources & evidence

ORD record
ord-4d6c7472585a41dc9fc61f42b25339a0
Source dataset
uspto-grants-1997_06
Patent number
US05639782

Reaction notes

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