7-[2-Hydroxy-5-(4-ethyl-3-hydroxyoct-1-enyl)-cyclopentyl]heptanoic acid → 7-[2-Hydroxy-5-(4-ethyl-3-hydroxyoctyl)cyclopentyl]heptanoic acid
Reaction equation
[OH:1][CH:2]1[CH2:6][CH2:5][CH:4]([CH:7]=[CH:8][CH:9]([OH:17])[CH:10]([CH2:15][CH3:16])[CH2:11][CH2:12][CH2:13][CH3:14])[CH:3]1[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][C:24]([OH:26])=[O:25].[H][H]>C(O)C.[Pd]>[OH:1][CH:2]1[CH2:6][CH2:5][CH:4]([CH2:7][CH2:8][CH:9]([OH:17])[CH:10]([CH2:15][CH3:16])[CH2:11][CH2:12][CH2:13][CH3:14])[CH:3]1[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][C:24]([OH:26])=[O:25]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
A stirred solution of 7-[2-hydroxy-5-(4-ethyl-3-hydroxyoct-1-enyl)-cyclopentyl]heptanoic acid [0.6 g; prepared as described in Example 4(iii)] in ethanol (25 ml.) was reduced with hydrogen at a hydrogen pressure of 6.3 kg./cm2 and in the presence of a 5% palladium on charcoal catalyst (0.68 g.). The catalyst was then filtered off and the filtrate evaporated to give 7-[2-hydroxy-5-(4-ethyl-3-hydroxyoctyl)cyclopentyl]heptanoic acid (0.47 g.), νmax 1700 cm-1 (Found: C, 71.2; H,11.7%; C22H42O4 requires C, 71.4; H, 11.4%). N.M.R. (approximately 10% solution in deuterochloroform) 0.65-1.05δ (2 overlapping triplets, terminal CH3 groups), 1.05-2.2δ (overlapping multiplets, cyclic and chain CH2 groups), 2.30δ (triplet CH2C=O),3.60-3.88δ, 4.2δ (multiplets, methylidene groups attached to hydroxy groups), 5.6-6.6δ broad singlet, OH and COOH groups).
Workup
- filtrationThe catalyst was then filtered off
- customthe filtrate evaporated
Sources & evidence
- ORD record
- ord-4704fa87822b4d80b930377dbf42cf5e
- Source dataset
- uspto-grants-1976_01
- Patent number
- US03935261
Reaction notes
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