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 2286072노트

반응식

HRID 2286072 반응식
[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

참가 물질

3

반응물 1

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

생성물 1

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

시약·촉매·용매 1

HCID 313Hydrochloric Acid용매

반응 조건

온도
60 °C

실험 절차

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%.

후처리

  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

출처 및 근거

ORD 기록
ord-43b22d9da22a4f58af64a800186427cd
출처 데이터셋
uspto-grants-1982_04
특허 번호
US04325967

반응 노트

불러오는 중…