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

HRID 1684044ノート

反応式

HRID 1684044 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]([CH:26]=[C:27]([I:31])[C:28]=1[O:29][CH3:30])[CH:24]=O.C1(C)C=CC(S([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[CH:22]=[C:23]([C@H:24]2[S:18][C@H:15]([C:5]3[CH:6]=[C:7]([O:13][CH3:14])[C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=3)[CH2:16][S:17]2)[CH:26]=[C:27]([I:31])[C:28]=1[O:29][CH3:30]

参加物

6

反応物 4

HCID 241BenzeneHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 27781133-Iodo-4,5-dimethoxybenzaldehydeHCID 190418081-(3,5-Dimethoxy-4-methoxymethoxyphenyl)-1,2-ethanedithiol

生成物 1

HCID 86750979trans 2-(3,4-Dimethoxy-5-iodophenyl)-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) (FIG. 19) (1.404 g,5.40 mmole), 3,4-dimethoxy-5-iodobenzaldehyde (41) (FIG. 22) (1.30 g, 4.45 mmole) and 0.542 g of pyridinium para-toluenesulfonate was added to 50 ml dry benzene and refluxed with Dean-Stark removal of the benzene- water azeotrope for 12 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 (2.38 g, 100%). The trans isomer can be isolated by recrystallization from methanol.

後処理

  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
  7. customThe trans isomer can be isolated by recrystallization from methanol

出典と根拠

ORDレコード
ord-1215ff9d9cf345bdb6fb6abc92213b61
出典データセット
uspto-grants-1997_06
特許番号
US05639782

反応ノート

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