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

HRID 1650048
ノート
印刷プレビュー

反応式

HRID 1650048 の反応式
[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
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 5

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 30318Osmium Tetroxide触媒HCID 3283Diethyl Ether溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-30e523b027464f0d88429f58537284d0
出典データセット
uspto-grants-1990_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04921994

反応ノート

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