Stannous Chloride → HCID 58280892, compound

HRID 405041

Reaction equation

HRID 405041 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

HCID 58280892HCID 58280892, compoundYield 75.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-3fe9d602865c4a60800fdf2eb4dfe9a2
Source dataset
uspto-grants-2014_06
Patent number
US08748739B2

Linked notes

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