3-Pentyn-2-ol, 1-(4-fluorophenoxy)-5-[(tetrahydro-2H-pyran-2-yl)oxy]-, 2-acetate → HCID 22759299, compound

HRID 1704345Notes

Reaction equation

HRID 1704345 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:21][C:22](=[O:24])[CH3:23])[CH2:12][O:13][C:14]1[CH:19]=[CH:18][C:17]([F:20])=[CH:16][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:21][C:22](=[O:24])[CH3:23])[CH2:12][O:13][C:14]1[CH:15]=[CH:16][C:17]([F:20])=[CH:18][CH:19]=1

Participants

5

Reactant 2

HCID 227592583-Pentyn-2-ol, 1-(4-fluorophenoxy)-5-[(tetrahydro-2H-pyran-2-yl)oxy]-, 2-acetateHCID 178418361HCID 178418361, compound

Product 1

HCID 22759299HCID 22759299, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

1-(2-Tetrahydropyranyloxy)-4-acetoxy-5-(4-fluorophenoxy)-2-pentyne (13.4 g.; 0.04 mole) is dissolved in ethyl acetate (100 ml.). 5% Palladium on carbon is added and the mixture is hydrogenated on the Parr apparatus at an initial pressure of 41 lbs./in2 and 25°. When 0.08 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 12.90 g.

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-f15b28c4dcfa47e59dd3423464992805
Source dataset
uspto-grants-1978_11
Patent number
US04126629

Reaction notes

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