Tetrahydrofuran → HCID 68905322, compound

HRID 1987703Notes

Reaction equation

HRID 1987703 reaction equation
[CH3:1][C:2]([CH3:20])([CH3:19])[C:3]#[C:4][C:5]1[S:6][C:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[N+:16]([O-])=O)=[CH:8][CH:9]=1.O1CCCC1>[Fe].C(O)(=O)C>[CH3:1][C:2]([CH3:20])([CH3:19])[C:3]#[C:4][C:5]1[S:6][C:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[NH2:16])=[CH:8][CH:9]=1

Participants

5

Reactant 2

HCID 8028TetrahydrofuranHCID 68903078HCID 68903078, compound

Product 1

HCID 68905322HCID 68905322, compound

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 2-(3,3-dimethyl-but-1-ynyl)-5-(2-nitro-phenyl)-thiophene (22 g, 76 mmol), tetrahydrofurane (100 ml) and acetic acid (425 ml of a 5% aqueous solution) was heated to 80° C. Iron powder (66 g, 1.2 mol) was added in small portions at this temperature. The reaction mixture was heated for 5 hours to reflux. After cooling, it was poured on ice and extracted with ethyl acetate. The combined organic layer was washed with brine, dried over magnesium sulfate and evaporated, delivering Compound No. 5.030.i (20 g).

Workup

  1. temperatureThe reaction mixture was heated for 5 hours
  2. temperatureto reflux
  3. temperatureAfter cooling
  4. additionit was poured on ice
  5. extractionextracted with ethyl acetate
  6. washThe combined organic layer was washed with brine
  7. dry with materialdried over magnesium sulfate
  8. customevaporated

Sources & evidence

ORD record
ord-58e012e939d0447eafc7a609dc973137
Source dataset
uspto-grants-2009_06
Patent number
US07553798B2

Reaction notes

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