Tetrahydrofuran → HCID 59560500, compound

HRID 1176179Notes

Reaction equation

HRID 1176179 reaction equation
C[Si]([C:5]#[C:6][C:7]1[C:15]2[C:11](=[N:12][S:13][N:14]=2)[CH:10]=[CH:9][CH:8]=1)(C)C.C([O-])([O-])=O.[K+].[K+].C1COCC1>CO>[C:6]([C:7]1[C:15]2[C:11](=[N:12][S:13][N:14]=2)[CH:10]=[CH:9][CH:8]=1)#[CH:5]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 11430Potassium CarbonateHCID 68407726HCID 68407726, compound

Product 1

HCID 59560500HCID 59560500, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4-(Trimethylsilyl)ethynylbenzo[c][1,2,5]-thiadiazole (0.100 g, 4.30×10−4 mol), K2CO3 (78.6 mg, 5.71×10−4 mol), THF (3 ml), and MeOH (2 ml) were added to a 25-ml Schlenk tube. The mixture was purged with N2 for 5 min, following which the reaction was stirred at room temperature for 1.5 h. The reaction mixture was then filtered, evaporated, and chromatographed on silica gel using 5:1 hexanes:THF as the eluent. Yield=63 g (91.4% based on 0.100 g of 4-(trimethylsilyl)ethynylbenzothiadiazole). 1H NMR (500 MHz, CDCl3): δ 8.01 (m, 1H, Ph-H), 7.78 (m, 1H, Ph-H), 7.56 (m, 1H, Ph-H), 3.56 (s, 1H, —CC—H).

Workup

  1. customThe mixture was purged with N2 for 5 min
  2. filtrationThe reaction mixture was then filtered
  3. customevaporated
  4. customchromatographed on silica gel using 5:1 hexanes

Sources & evidence

ORD record
ord-998aafdc00d244c798f7d46b5ac91a75
Source dataset
uspto-grants-2010_11
Patent number
US07842758B2

Reaction notes

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