Acetylene → HCID 13135222, compound

HRID 262426Notes

Reaction equation

HRID 262426 reaction equation
[CH2:1]([Mg]Br)[CH3:2].C#C.[CH3:7][O:8][CH:9]1[C:18]2[CH:17]=[CH:16][C:15](=[O:19])[CH2:14][C:13]=2[CH:12]([O:20][CH3:21])[CH2:11][CH2:10]1>O1CCCC1>[CH3:7][O:8][C:9]1[C:18]2[CH2:17][CH2:16][C:15]([C:1]#[CH:2])([OH:19])[CH2:14][C:13]=2[C:12]([O:20][CH3:21])=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 6326Acetylene2×HCID 70490705HCID 70490705, compoundHCID 178418443HCID 178418443, compound2×

Product 1

HCID 13135222HCID 13135222, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Acetylene, purified by passing it first through a dry ice acetone trap, then through concentrated sulfuric acid, was bubbled rapidly through freshly distilled tetrahydrofuran (20 ml) under nitrogen for one hour. Ethylmagnesium bromide (50 ml, 3.15 M in ether, 15.8 mmole) was added slowly. The temperature was maintained between 28°-33° C. by cooling with a water bath. After the complete addition of ethylmagnesium bromide, the passage of the acetylene gas was continued and 1,4-dimethoxy-6-tetralone (XIII) (1.03 g, 5 mmole) in dry tetrahydrofuran (5,0 ml) was added with stirring. After addition, the passage of the acetylene was continued for an extra one hour and the reaction mixture was left stirring at room temperature overnight. The reaction mixture was quenched with saturated oxalic acid and extracted with chloroform. The chloroform extract was washed well with water, dried over anhydrous magnesium sulfate, and evaporated to dryness. The oil residue was triturated with ether to give 1,4-dimethoxy-6-ethynyl-6-hydroxy-5,8-dihydro-(7H)naphthalene (XIV) as a white solid, m.p. 103°-105° C. (ethanol).

Workup

  1. customAcetylene, purified
  2. customthrough concentrated sulfuric acid, was bubbled rapidly through freshly distilled tetrahydrofuran (20 ml) under nitrogen for one hour
  3. temperatureThe temperature was maintained between 28°-33° C.
  4. temperatureby cooling with a water bath
  5. additionAfter addition
  6. waitthe reaction mixture was left
  7. stirringstirring at room temperature overnight
  8. customThe reaction mixture was quenched with saturated oxalic acid
  9. extractionextracted with chloroform
  10. extractionThe chloroform extract
  11. washwas washed well with water
  12. dry with materialdried over anhydrous magnesium sulfate
  13. customevaporated to dryness
  14. customThe oil residue was triturated with ether

Sources & evidence

ORD record
ord-345ed8d87cba48398c9d76b40f4c523f
Source dataset
uspto-grants-1979_05
Patent number
US04154745

Reaction notes

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