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 372059ノート

反応式

HRID 372059 の反応式
[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

参加物

3

反応物 1

HCID 205429127-(3-Cyclohexyl-3-oxopropyl)-6-(7-hydroxyheptyl)-1,4-dioxaspiro[4,4]nonane

生成物 1

HCID 205428857-[2-(3-Cyclohexyl-3-oxopropyl)-5-oxocyclopentyl]heptan-1-ol収率 36.2%

試薬・触媒・溶媒 1

HCID 313Hydrochloric Acid溶媒

反応条件

温度
60 °C

実験手順

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; 1N) 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%.

後処理

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

出典と根拠

ORDレコード
ord-a41fef6fbe1841e3bd2cf59a7edc0908
出典データセット
uspto-grants-1978_05
特許番号
US04088695

反応ノート

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