HCID 21317646, compound → HCID 21317564, compound

HRID 328798Notes

Reaction equation

HRID 328798 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH2:8][C:9]#[C:10][CH:11]([O:24][C:25](=[O:27])[CH3:26])[CH2:12][O:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:23])([F:22])[F:21])[CH:15]=1.[H][H]>C(OCC)(=O)C.[Pd]>[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH2:8][CH2:9][CH2:10][CH:11]([O:24][C:25](=[O:27])[CH3:26])[CH2:12][O:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:23])([F:22])[F:21])[CH:15]=1

Participants

5

Reactant 2

HCID 21317646HCID 21317646, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 21317564HCID 21317564, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

1-(2-Tetrahydropyranyloxy)-4-acetoxy-5-(3-trifluoromethylphenoxy)-2-pentyne (40.18 g.; 0.104 mole) is dissolved in ethyl acetate (200 ml.). 5% Palladium on carbon (5 g.) is added and the mixture is hydrogenated on the Parr apparatus at an initial pressure of 45 lbs./in2 and 25°. When 0.208 mole of hydrogen is absorbed, the catalyst is removed by filtration and the solvent is evaporated under vacuum to give the title compound as a light orange residual oil, yield 40.60 g.; pmr (CDCl3) δ 2.13 (3H, s CH3COO), 4.10 (2H, d CH2O), 5.20 (1H, m CHOCO), 7.22 (4H, m Aryl H).

Workup

  1. custom/in2 and 25°
  2. customthe catalyst is removed by filtration
  3. customthe solvent is evaporated under vacuum

Sources & evidence

ORD record
ord-7a597d3e59c5414bba535b8c42ec4543
Source dataset
uspto-grants-1977_04
Patent number
US04018802

Reaction notes

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