8-Methylsulfonyl-12-benzyloxy-13-(4-fluorophenoxy)tridecanoic acid → 8-Methylsulfonyl-12-hydroxy-13-(4-fluorophenoxy)tridecanoic acid

HRID 1833482Notes

Reaction equation

HRID 1833482 reaction equation
[CH3:1][S:2]([CH:5]([CH2:15][CH2:16][CH2:17][CH:18]([O:28]CC1C=CC=CC=1)[CH2:19][O:20][C:21]1[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=1)[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]([OH:14])=[O:13])(=[O:4])=[O:3]>C(O)C.[Pd]>[CH3:1][S:2]([CH:5]([CH2:15][CH2:16][CH2:17][CH:18]([OH:28])[CH2:19][O:20][C:21]1[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=1)[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]([OH:14])=[O:13])(=[O:4])=[O:3]

Participants

4

Reactant 1

HCID 213175768-Methylsulfonyl-12-benzyloxy-13-(4-fluorophenoxy)tridecanoic acid

Product 1

HCID 213175788-Methylsulfonyl-12-hydroxy-13-(4-fluorophenoxy)tridecanoic acidYield 91%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

The hydrogenolysis of 8-methylsulfonyl-12-benzyloxy-13-(4-fluorophenoxy)tridecanoic acid (1.237 g., 2.43 mmoles) in absolute ethanol (100 ml.) in the presence of 10% palladium on charcoal (0.2 g.) is carried out at 25° C. in an atmospheric-pressure hydrogenator. After hydrogen uptake stops, the catalyst is filtered off and the solvent is evaporated in vacuo to leave the title compound as a colorless oil (0.927 g., 2.21 mmoles, 91%). ir (neat) 2.8~4.0, 5.81, 6.22, 6.65, 6.86, 7.80, 8.30, 8.95, 10.46, 12.04, 13.18μ; pmr (CDCl3)δ1.1-3.0 (22H, m, containing a methyl singlet at 2.82δ), 3.6-4.2 (3H, m), 6.2-6.7 (2H, m), 6.7-7.2 (4H, m).

Workup

  1. customis carried out at 25° C. in an atmospheric-pressure hydrogenator
  2. filtrationAfter hydrogen uptake stops, the catalyst is filtered off
  3. customthe solvent is evaporated in vacuo

Sources & evidence

ORD record
ord-cc17840c13524149acaa4bf98df7335a
Source dataset
uspto-grants-1978_01
Patent number
US04066675

Reaction notes

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