4-{3-[3-[3-(1-Hydroxycyclohexyl)-2-propynyl]-4-oxo-2-thiazolidinyl]propyl}benzoic acid → 4-{3-[3-[3-(1-Hydroxycyclohexyl)-(Z)-2-propenyl]-4-oxo-2-thiazolidinyl]propyl}benzoic Acid

HRID 28218Notes

Reaction equation

HRID 28218 reaction equation
[OH:1][C:2]1([C:8]#[C:9][CH2:10][N:11]2[C:15](=[O:16])[CH2:14][S:13][CH:12]2[CH2:17][CH2:18][CH2:19][C:20]2[CH:28]=[CH:27][C:23]([C:24]([OH:26])=[O:25])=[CH:22][CH:21]=2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.[H][H]>C(OCC)(=O)C.[Pd]>[OH:1][C:2]1(/[CH:8]=[CH:9]\[CH2:10][N:11]2[C:15](=[O:16])[CH2:14][S:13][CH:12]2[CH2:17][CH2:18][CH2:19][C:20]2[CH:21]=[CH:22][C:23]([C:24]([OH:26])=[O:25])=[CH:27][CH:28]=2)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7]1

Participants

5

Reactant 2

HCID 204459924-{3-[3-[3-(1-Hydroxycyclohexyl)-2-propynyl]-4-oxo-2-thiazolidinyl]propyl}benzoic acidHCID 178418361HCID 178418361, compound

Product 1

HCID 867372414-{3-[3-[3-(1-Hydroxycyclohexyl)-(Z)-2-propenyl]-4-oxo-2-thiazolidinyl]propyl}benzoic Acid

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

4-{3-[3-[3-(1-Hydroxycyclohexyl)-2-propynyl]-4-oxo-2-thiazolidinyl]propyl}benzoic acid (4.0 g., 0.01 mole) is dissolved in ethyl acetate (50 ml.) and hydrogenated at 25° C. and one atmosphere pressure over 1.0 g. of a 5% palladium on charcoal catalyst. The theoretical amount (0.01 mole) of hydrogen is absorbed in 110 minutes. The catalyst is removed by filtration and the solvent evaporated. The residual oil is chromatographed on 60 g. of silica gel with elution by 2% methanol is chloroform. The chromatographed product crystallizes and is recrystallized from butyl chloride to yield 1.4 g. of the title product, m.p. 118°-120° C.; pmr (CDCl3) δ5.14 (1H, m, --CH2 --CH=), 5.60 (1H, d, ##STR46##

Workup

  1. customThe catalyst is removed by filtration
  2. customthe solvent evaporated
  3. customThe residual oil is chromatographed on 60 g
  4. washof silica gel with elution by 2% methanol
  5. customThe chromatographed product crystallizes
  6. customis recrystallized from butyl chloride
  7. customto yield 1.4 g

Sources & evidence

ORD record
ord-41bb0dd0ecad4270963accd5a9391572
Source dataset
uspto-grants-1980_09
Patent number
US04225609

Reaction notes

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