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

HRID 242763노트

반응식

HRID 242763 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-3dd499004e4042c3a1599452eb6b739c
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08653228B2

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