Quinoline → HCID 10419313, compound

HRID 971839Notes

Reaction equation

HRID 971839 reaction equation
[CH3:1][Si:2]([CH3:9])([CH3:8])[C:3]#[C:4][CH:5]([OH:7])[CH3:6].N1C2C(=CC=CC=2)C=CC=1.[H][H]>[Pd].C1C=CC=CC=1>[CH3:1][Si:2]([CH3:9])([CH3:8])/[CH:3]=[CH:4]\[CH:5]([OH:7])[CH3:6]

Participants

6

Reactant 3

HCID 7047QuinolineHCID 27608284-(Trimethylsilyl)but-3-yn-2-olHCID 178418361HCID 178418361, compound

Product 1

HCID 10419313HCID 10419313, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 241BenzeneSolvent

Procedure

A solution of 94.15 parts by weight of 4-(trimethylsilyl)-3-butyn-2-ol (II) in 940 parts by volume of benzene and 4.7 parts by volume of quinoline is hydrogenated at a constant pressure of 2 p.s.i. in the presence of 9.4 parts by weight of 5% palladium on barium sulfate until one equivalent of hydrogen is consumed. The catalyst is removed and the solution is washed twice with 100 parts per volume of 5% aqueous hydrochloric acid and then with water. After drying over sodium sulfate, the solvent is removed and the residue is distilled at 33°-39° C./0.3 mm to give cis-4-(trimethylsilyl)-3-buten-2-ol (III) which has the following structural formula: ##STR9##

Workup

  1. customThe catalyst is removed
  2. washthe solution is washed twice with 100 parts per volume of 5% aqueous hydrochloric acid
  3. dry with materialAfter drying over sodium sulfate
  4. customthe solvent is removed
  5. distillationthe residue is distilled at 33°-39° C./0.3 mm

Sources & evidence

ORD record
ord-afb8b828a19f49ac893cc2572d30c87a
Source dataset
uspto-grants-1979_07
Patent number
US04161480

Reaction notes

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