HCID 20373756, compound → HCID 54256320, compound

HRID 1834662Notes

Reaction equation

HRID 1834662 reaction equation
[OH:1][CH:2]([CH:10]1[CH2:14][CH2:13][C:12](=[O:15])[CH:11]1[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22]([OH:24])=[O:23])[C:3]#[C:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9]>C(OCC)(=O)C.[Pd].CC([O-])=O.CC([O-])=O.[Pb+2]>[OH:1][CH:2]([C@H:10]1[CH2:14][CH2:13][C:12](=[O:15])[C@H:11]1[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22]([OH:24])=[O:23])[CH:3]=[CH:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9]

Participants

4

Reactant 1

HCID 20373756HCID 20373756, compound

Product 1

HCID 54256320HCID 54256320, compound

Reagents, catalysts & solvents 2

HCID 131709914Lindlars catalystCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2-(1-hydroxy-2-octynyl)-5-oxocyclopentaneheptanoic acid (1.12 g), described in Example 3, in 20 ml of ethyl acetate is subjected to hydrogenation with Lindlar catalyst (200 mg) to yield the title compound which is purified by chromatography on silica gel. [Lindlar catalyst is a mixture of palladium and lead oxide on calcium carbonate, H. Lindlar, Helv. Chim. Acta, 35, 446 (1952)]. The title compound has νmaxfilm (broad OH absorption) 1730, 1710 cm-1 ; nmr (CDCl3) δ 5.54 (m, 2H), 7.14 (broad, 2H).

Sources & evidence

ORD record
ord-61e6724622ca451891bc6311491d2084
Source dataset
uspto-grants-1978_01
Patent number
US04070482

Reaction notes

Loading…