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Water → Trans-3-[2-Benzyloxy-4-(1,1-dimethylheptyl)phenyl]-4-(2-oxoethyl)cyclohexanone ethylene ketal

HRID 1758152
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HRID 1758152 반응식
[CH2:1]1O[C:4]2([CH2:9][CH2:8][C@@H:7]([CH2:10][CH:11]=C)[C@H:6]([C:13]3[CH:18]=[CH:17][C:16]([C:19]([CH3:27])([CH3:26])[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])=[CH:15][C:14]=3[O:28][CH2:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[CH2:5]2)[O:3][CH2:2]1.I([O-])(=O)(=O)=[O:38].[Na+].O1CCCC1.S([O-])([O-])=O.[Na+].[Na+].[OH2:54]>[Os](=O)(=O)(=O)=O.CCOCC>[CH2:2]1[O:3][C:4]2([CH2:9][CH2:8][C@@H:7]([CH2:10][CH:11]=[O:38])[C@H:6]([C:13]3[CH:18]=[CH:17][C:16]([C:19]([CH3:26])([CH3:27])[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])=[CH:15][C:14]=3[O:28][CH2:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[CH2:5]2)[O:54][CH2:1]1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 5

HCID 962WaterHCID 8028TetrahydrofuranHCID 24437Sodium SulfiteHCID 23667635Sodium periodateHCID 86738780Trans-3-[2-Benzyloxy-4-(1,1-dimethylheptyl)phenyl]-4-(2-propenyl)cyclohexanone ethylene ketal

생성물 1

HCID 86738782Trans-3-[2-Benzyloxy-4-(1,1-dimethylheptyl)phenyl]-4-(2-oxoethyl)cyclohexanone ethylene ketal
수율 59%

시약·촉매·용매 2

HCID 30318Osmium Tetroxide촉매HCID 3283Diethyl Ether용매

실험 절차

A mixture of 17.0 g. (34.7 mmoles) of trans-3-[2-benzyloxy-4-(1,1-dimethylheptyl)phenyl]-4-(2-propenyl)cyclohexanone ethylene ketal, 44.5 g. (0.208 mmole) of sodium metaperiodate and 176 mg. (0.69 mmole) of osmium tetroxide in 340 ml. tetrahydrofuran and 100 ml. of water was stirred at room temperature for 3.5 hours. The reaction mixture was then added to 1000 ml. 15% sodium sulfite-1000 ml. ether. The organic phase was separated, washed twice with 500 ml. of saturated sodium bicarbonate, dried over magnesium sulfate and evaporated (aspirator). The residue was purified by column chromatography on 400 g. of silica gel eluted with 33-75% ether-petroleum ether to yield 10.0 g. (59%) of the title compound as an oil.

후처리

  1. additionA mixture of 17.0 g
  2. additionThe reaction mixture was then added to 1000 ml
  3. customThe organic phase was separated
  4. washwashed twice with 500 ml
  5. dry with materialof saturated sodium bicarbonate, dried over magnesium sulfate
  6. customevaporated (aspirator)
  7. customThe residue was purified by column chromatography on 400 g
  8. washof silica gel eluted with 33-75% ether-petroleum ether
  9. customto yield 10.0 g

출처 및 근거

ORD 기록
ord-2185a99c054649f3ae34433c4d466b4f
출처 데이터셋
uspto-grants-1983_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04371720

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