8-methylsulfonyl-12(S)-hydroxy-10-heptadecynoic acid → 8-methylsulfonyl-12(S)-hydroxyheptadecanoic acid

HRID 328780Notes

Reaction equation

HRID 328780 reaction equation
[CH3:1][S:2]([CH:5]([CH2:15][C:16]#[C:17][C@@H:18]([OH:24])[CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]([OH:14])=[O:13])(=[O:4])=[O:3].[H][H]>C(OCC)(=O)C.C1CCCCC1.[Pt]>[CH3:1][S:2]([CH:5]([CH2:15][CH2:16][CH2:17][C@@H:18]([OH:24])[CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]([OH:14])=[O:13])(=[O:3])=[O:4]

Participants

6

Reactant 2

HCID 227969758-methylsulfonyl-12(S)-hydroxy-10-heptadecynoic acidHCID 178418361HCID 178418361, compound2×

Product 1

HCID 227969768-methylsulfonyl-12(S)-hydroxyheptadecanoic acid

Reagents, catalysts & solvents 3

HCID 23939PlatinumCatalystHCID 8078CyclohexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

8-Methylsulfonyl-12(S)-hydroxy-10-heptadecynoic acid (36.0 g., 0.10 mole) and 5% platinum-on-charcola catalyst (4.0 g.) are placed in a mixture of ethyl acetate (100 ml.) and cyclohexane (200 ml.) and hydrogenated in a Parr apparatus with an initial hydrogen pressure of 45 pounds per square inch. The uptake of the required 0.2 mole of hydrogen is complete in 20 minutes. The catalyst is removed by filtration and the solvents evaporated to leave the product as a residual oil weighing 33.5 g. It is purified by chromatography on silica gel with benzene-dioxane-acetic acid elution. The title compound is obtained as a nearly colorless viscous oil.

Workup

  1. customThe catalyst is removed by filtration
  2. customthe solvents evaporated

Sources & evidence

ORD record
ord-da0b695f55a74014a0db9bf382879102
Source dataset
uspto-grants-1977_04
Patent number
US04018802

Reaction notes

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