Stannous Chloride → HCID 58280892, 화합물

HRID 405041

반응식

HRID 405041 반응식
[S:1]1[CH:5]=[CH:4][C:3]2[C:6](=O)[C:7]3[S:8][CH:9]=[CH:10][C:11]=3[C:12](=O)[C:2]1=2.[CH2:15]([Mg]Br)[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22].Cl[Sn]Cl>C1COCC1>[CH2:15]([C:6]1[C:7]2[S:8][CH:9]=[CH:10][C:11]=2[C:12]([CH2:5][CH2:4][CH2:3][CH2:2][CH2:12][CH2:11][CH2:7][CH3:6])=[C:2]2[S:1][CH:5]=[CH:4][C:3]=12)[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]

참가 물질

5

반응물 3

HCID 24479Stannous ChlorideHCID 288478(Benzo(1,2-b:4,5-b)dithiophene-4,8-dione)HCID 178443577HCID 178443577, 화합물

생성물 1

HCID 58280892HCID 58280892, 화합물수율 75.2%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a 100 mL flask under nitrogen was added 4,8-dihydrobenzo[1,2-b:4,5-b′]dithiophene-4,8-dione (1.1 g, 5.0 mmol) and anhydrous THF (10 mL). The mixture was heated to reflux and octylmagnesium bromide (20 mmol, 10 mL, 2.0 M in Et2O) was added dropwise. After refluxing for 2 hours more, SnCl2 solution (7.3 g in 19 mL 10% HCl) was slowly added dropwise. The mixture was kept at 60° C. for 1 hour. After cooling down, the organic phase was separated. The water phase was extracted with ether once and the organic phases were combined and dried over Na2SO4. Purification by column chromatography with hexane as eluent gave a yellow oil (780 mg, yield 37.6%). 1H NMR (CDCl3, 500 MHz) δ=7.48 (d, J=5.5 Hz, 2H), 7.47 (d, J=5.5 Hz, 2H), 3.20 (t, J=7.5 Hz, 4H), 1.75-1.88 (m, 4H), 1.43-1.54 (m, 4H), 1.21-1.42 (bs, 16H), 0.90 (t, J=7.0 Hz, 6H).

후처리

  1. temperatureThe mixture was heated
  2. temperatureto reflux
  3. temperatureAfter refluxing for 2 hours more
  4. temperatureAfter cooling down
  5. customthe organic phase was separated
  6. extractionThe water phase was extracted with ether once
  7. dry with materialdried over Na2SO4
  8. customPurification by column chromatography with hexane as eluent

출처 및 근거

ORD 기록
ord-3fe9d602865c4a60800fdf2eb4dfe9a2
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08748739B2

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