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

HRID 1684042ノート

反応式

HRID 1684042 の反応式
[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

参加物

6

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 22272175Benzene--water (1/1)溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-f30857b31f09454289a06d733e918ece
出典データセット
uspto-grants-1997_06
特許番号
US05639782

反応ノート

読み込み中…