Sodium Sulfide → Methyl 4,6-dihydrothieno[3,4-b]thiophene-2-carboxylate

HRID 242763ノート

反応式

HRID 242763 の反応式
[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([CH2:12]Cl)=[C:8]([CH2:10]Cl)[CH:9]=1)=[O:4].[S-2:14].[Na+].[Na+]>CO>[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]2[CH2:12][S:14][CH2:10][C:8]=2[CH:9]=1)=[O:4]

参加物

4

反応物 2

HCID 14804Sodium SulfideHCID 11096691Methyl 4,5-bis(chloromethyl)thiophene-2-carboxylate

生成物 1

HCID 3441857Methyl 4,6-dihydrothieno[3,4-b]thiophene-2-carboxylate収率 50%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒2 回

実験手順

A solution of 4.8 g (20 mmol) (2) in 240 mL methanol was heated up and kept mild boiling. Sodium sulfide solution (1.7 g, 22 mmol) in 160 mL methanol was added dropwise in 2 h. After cooling of the reaction mixture, the precipitate was filtered off. The solvent was removed by evaporation and the residue was washed by water. Column chromatography on silica gel using dichloromethane yielded the pure title compound as a white solid 2.0 g (50%). 1HNMR (CDCl3): δ 3.87 (3H, s), 4.05-4.06 (2H, t, J=3 Hz), 4.19-4.20 (2H, t, J=3 Hz), 7.48 (1H, s). 13CNMR (CDCl3): δ33.12, 33.47, 52.19, 127.90, 137.30, 143.90, 146.64, 162.51.

後処理

  1. temperatureAfter cooling of the reaction mixture
  2. filtrationthe precipitate was filtered off
  3. customThe solvent was removed by evaporation
  4. washthe residue was washed by water

出典と根拠

ORDレコード
ord-3dd499004e4042c3a1599452eb6b739c
出典データセット
uspto-grants-2014_02
特許番号
US08653228B2

反応ノート

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