Acetylene → HCID 13116850, compound

HRID 2164605Notes

Reaction equation

HRID 2164605 reaction equation
C#C.[CH3:3][C:4]([O-])(C)C.[K+].[F:9][C:10]1[CH:28]=[CH:27][C:13]([O:14][CH:15]([N:22]2[CH:26]=[N:25][CH:24]=[N:23]2)[C:16](=[O:21])[C:17]([CH3:20])([CH3:19])[CH3:18])=[CH:12][CH:11]=1.[Cl-].[NH4+]>O1CCCC1>[F:9][C:10]1[CH:11]=[CH:12][C:13]([O:14][CH:15]([N:22]2[CH:26]=[N:25][CH:24]=[N:23]2)[C:16]([OH:21])([C:17]([CH3:19])([CH3:20])[CH3:18])[C:3]#[CH:4])=[CH:27][CH:28]=1

Participants

6

Reactant 4

HCID 6326Acetylene2×HCID 25517Ammonium ChlorideHCID 13021654HCID 13021654, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 13116850HCID 13116850, compoundYield 44.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Acetylene was passed into a suspension of 31.4 g (0.28 mol) of potassium tert-butylate in 300 ml of tetrahydrofuran for 30 minutes at 15° C., while stirring. A solution of 55.5 g (0.2 mol) of 1-(4-fluorophenoxy)-3,3-dimethyl-1-(1H-1,2,4-triazol-1-yl)-butan-2-one in 150 ml of tetrahydrofuran was then added dropwise in the course of one hour, while acetylene was further passed through the mixture. After a further two hours, the solution was adjusted to a pH value of 8 by the addition of 175 ml of a 23% strength aqueous ammonium chloride solution. The mixture was extracted with twice 200 ml of ethyl acetate, the extracts were washed with water, and the solution was concentrated under reduced pressure. The remaining solid residue was triturated with petroleum ether. 27.2 g (44.8% of theory) of 3-((4-fluorophenoxy)-(1H-1,2,4-triazol-1-yl)-methyl)-4,4-dimethyl-pent-1-yn-3-ol of melting point 155° to 161° C. were thus obtained. By cooling and triturating, a further 3.2 g (5.3% of theory) of a pure diastereomeric form A of melting point 134° to 135° C. were obtained from the petroleum ether phase.

Workup

  1. extractionThe mixture was extracted with twice 200 ml of ethyl acetate
  2. washthe extracts were washed with water
  3. concentrationthe solution was concentrated under reduced pressure
  4. customThe remaining solid residue was triturated with petroleum ether

Sources & evidence

ORD record
ord-27ae4d33fbbc49909e4bd781a09dd61a
Source dataset
uspto-grants-1985_03
Patent number
US04505922

Reaction notes

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