HCID 4158166, compound → 2-(Chloroethynyl)-5-nitrofuran

HRID 2398098Notes

Reaction equation

HRID 2398098 reaction equation
[Cl:1][C:2](Cl)=[CH:3][C:4]1[O:5][C:6]([N+:9]([O-:11])=[O:10])=[CH:7][CH:8]=1.CC(C)([O-])C.[K+]>C(O)(C)(C)C>[Cl:1][C:2]#[C:3][C:4]1[O:5][C:6]([N+:9]([O-:11])=[O:10])=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 4158166HCID 4158166, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 214347412-(Chloroethynyl)-5-nitrofuran

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent2×

Procedure

To a stirred solution of 20.8 g of 1 in 100 ml of dry tert-butanol was added dropwise at 5°-10° over a 30-minute period a solution of 11.2 g of potassium tert-butoxide in 100 ml of tert-butanol. The mixture then was stirred at 5°-10° for 1 hour longer. Concentration of the mixture under reduced pressure gave a dark residue which was extracted with ether and water. The ether phase was separated, dried over magnesium sulfate and Claisen distilled to give 4 as a liquid, b.p.: 73°-76° at 0.2 torr which solidified on standing, the solid having a melting point of 38°-41°.

Workup

  1. customConcentration of the mixture under reduced pressure gave a dark residue which
  2. extractionwas extracted with ether and water
  3. customThe ether phase was separated
  4. dry with materialdried over magnesium sulfate and Claisen
  5. distillationdistilled

Sources & evidence

ORD record
ord-be08813211e54a99922aeac92e8742b8
Source dataset
uspto-grants-1977_05
Patent number
US04024161

Reaction notes

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