7-(3-Cyclohexyl-3-oxopropyl)-6-(7-hydroxyheptyl)-1,4-dioxaspiro[4,4]nonane → 7-[2-(3-Cyclohexyl-3-oxopropyl)-5-oxocyclopentyl]heptan-1-ol

HRID 2052329Notes

Reaction equation

[CH:1]1([C:7](=[O:27])[CH2:8][CH2:9][CH:10]2[CH2:18][CH2:17][C:12]3(OCC[O:13]3)[CH:11]2[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][OH:26])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1>Cl>[CH:1]1([C:7](=[O:27])[CH2:8][CH2:9][CH:10]2[CH2:18][CH2:17][C:12](=[O:13])[CH:11]2[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][OH:26])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of 7-(3-cyclohexyl-3-oxopropyl)-6-(7-hydroxyheptyl)-1,4-dioxaspiro[4,4]nonane (0.5 g.) in hydrochloric acid (20 ml; 1 N) was stirred at 60° C. for 2 hours, cooled to ambient temperature and extracted with diethyl ether. The ethereal extract was washed with water, then dried over sodium sulphate. Removal of the solvent under reduced pressure gave a crude product (0.4 g.) which was purified by preparative thin layer chromatography on silica gel, using a mixture of diethyl ether, ethyl acetate and hexane (2:1:1 v/v) as eluant, to give 7-[2-(3-cyclohexyl-3-oxopropyl)-5-oxocyclopentyl]heptan-1-ol (0.16 g.), νmax 3450 cm-1, 1730 cm-1, 1700 cm-1, 1060 cm-1 ; Elemental analysis: Found: C, 74.6; H, 10.7%; C21H36O3 requires C, 74.95; H, 10.78%.

Workup

temperaturecooled to ambient temperature
extractionextracted with diethyl ether
extractionThe ethereal extract
washwas washed with water
dry with materialdried over sodium sulphate
customRemoval of the solvent under reduced pressure
customgave a crude product (0.4 g.) which
customwas purified by preparative thin layer chromatography on silica gel
additiona mixture of diethyl ether, ethyl acetate and hexane (2:1:1 v/v) as eluant

Sources & evidence

ORD record: ord-bbf857f1d85d4185a3aae2f48912db37
Source dataset: uspto-grants-1980_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04183870

Reaction notes

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