Hydrochloric Acid → HCID 3126015, compound

HRID 2059290Notes

Reaction equation

HRID 2059290 reaction equation
[CH:1]#[CH:2].[C:3]([C:11]1[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=1)(=[O:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.Cl>O1CCCC1>[C:4]1([C:3]([C:11]2[CH:12]=[CH:13][N:14]=[CH:15][CH:16]=2)([OH:10])[C:1]#[CH:2])[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6326Acetylene2×HCID 267314-Benzoylpyridine

Product 1

HCID 3126015HCID 3126015, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Acetylene was passed into a suspension of 174 g (1.55 mol) of potassium tert.-butylate in 750 ml of tetrahydrofuran for about 30 minutes. 198 g (1.08 mol) of 4-benzoylpyridine in 400 ml of tetrahydrofuran were added dropwise to this reaction mixture, acetylene being simultaneously passed in for about a further hour. The mixture was subsequently stirred for 30 minutes, dilute hydrochloric acid was added, the salt which had precipitated was filtered off and the organic phase of the filtrate was separated off. This phase was concentrated in vacuo. The solid residue was triturated with water and the solid was filtered off and washed with methanol/water (1:1). 170 g (75% of theory) of 3-phenyl-3-pyridin-4-yl-1-propyn-3-ol of melting point 165°-66° C. were obtained.

Workup

  1. customthe salt which had precipitated
  2. filtrationwas filtered off
  3. customthe organic phase of the filtrate was separated off
  4. concentrationThis phase was concentrated in vacuo
  5. customThe solid residue was triturated with water
  6. filtrationthe solid was filtered off
  7. washwashed with methanol/water (1:1)

Sources & evidence

ORD record
ord-028f317cb11b45a0b0e72f8fbebcbcf9
Source dataset
uspto-grants-1982_03
Patent number
US04322442

Reaction notes

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