Stannous Chloride → HCID 86636741, compound

HRID 423443Notes

Reaction equation

HRID 423443 reaction equation
[Sn](Cl)Cl.[CH3:4][Si:5]([CH3:35])([CH3:34])[C:6]1(O)[C:17]2[C:16]3[CH:18]=[CH:19][CH:20]=[CH:21][C:15]=3[S:14][C:13]=2[C:12]([Si:23]([CH3:26])([CH3:25])[CH3:24])(O)[C:11]2[C:10]3[C:27]([C:31]#[CH:32])=[CH:28][CH:29]=[CH:30][C:9]=3[S:8][C:7]1=2>C(O)(=O)C.CC(C)=O>[CH3:4][Si:5]([CH3:34])([CH3:35])[C:6]1[C:17]2[C:16]3[CH:18]=[CH:19][CH:20]=[CH:21][C:15]=3[S:14][C:13]=2[C:12]([Si:23]([CH3:24])([CH3:25])[CH3:26])=[C:11]2[C:7]=1[S:8][C:9]1[CH:30]=[CH:29][CH:28]=[C:27]([C:31]#[CH:32])[C:10]=12

Participants

5

Reactant 2

HCID 24479Stannous ChlorideHCID 86636742HCID 86636742, compound

Product 1

HCID 86636741HCID 86636741, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 180AcetoneSolvent

Conditions

Temperature
2.5 °C

Procedure

A solution of tin(II)chloride dehydrate (3.11 g, 9.2 mmol) in 50% acetic acid (50 ml) is added within ten minutes to a solution of 6,12-bis-trimethylsilanylethynyl-6,12-dihydro-dibenzo[d,d′]benzo[1,2-b;4,5-b′]dithiophene-6,12-diol (educt 5) (3.1 g, 6 mmol) in acetone (45 ml). There is a slight temperature increase (2-3° C.), and formation of a yellow suspension. This suspension is stirred over night at ambient temperature, and then the solid is filtered off. The solid is then washed with 50% acetic acid (twice with 30 ml), water (twice with 40 ml), and acetone (2*50 ml). The residue is then dried to give crude product which is filtered over a pad of silica (60 g) with chloroform to give product which is recrystallised from chloroform (35 ml). The product is filtered off, washed with chloroform (10 ml), and hexane (20 ml). After drying, the title product is obtained as yellow crystals. Mp. (DSC) 278° C. and 285° C. 1H-NMR (CDCl3, 300 MHz) δ 0.49 (s, 9H, SiCH3); 7.48-7.56 (m, 2H, H-2, H-3), 7.91 (d, 1H, H-4); 9.20 (d, 1H, H-1). 13C-NMR (CDCl3, 75 MHz) δ 0.28 (CH3); 101.79, 109.51 (C≡C); 112.56 (C-6); 122.93 (C-4); 124.66 (C-2); 125.14 (C-1); 127.72 (C-3); 132.91 (C-6a); 136.63 (C-6b); 140.73 (C-4-a); 143.11 (C-5a).

Workup

  1. filtrationthe solid is filtered off
  2. washThe solid is then washed with 50% acetic acid (twice with 30 ml), water (twice with 40 ml), and acetone (2*50 ml)
  3. customThe residue is then dried
  4. customto give crude product which
  5. filtrationis filtered over a pad of silica (60 g) with chloroform
  6. customto give product which
  7. customis recrystallised from chloroform (35 ml)
  8. filtrationThe product is filtered off
  9. washwashed with chloroform (10 ml), and hexane (20 ml)
  10. customAfter drying

Sources & evidence

ORD record
ord-3f74a16bc8c0484fa205a6d120f167dc
Source dataset
uspto-grants-2012_01
Patent number
US08101776B2

Reaction notes

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