Water → cis-1,2-Cyclooctanediol

HRID 459479ノート

反応式

HRID 459479 の反応式
[CH:1]1CC[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1.C[N+]1([O-])[CH2:15][CH2:14][O:13]CC1.[OH2:17]>C(#N)C.[Os](=O)(=O)(=O)=O>[C@@H:14]1([OH:13])[CH2:15][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][C@@H:1]1[OH:17]

参加物

6

反応物 3

HCID 962WaterHCID 136091-CycloocteneHCID 82029Methyl morpholine oxide

生成物 1

HCID 10888034cis-1,2-Cyclooctanediol

試薬・触媒・溶媒 2

HCID 30318Osmium Tetroxide触媒HCID 6342Acetonitrile溶媒

反応条件

温度
45 °C

実験手順

Cyclooctene (4.41 g) was dissolved in acetonitrile (45 ml) and water (15 ml), and to the solution N-methylmorpholine N-oxide (5.15 g) and microcapsulated osmium tetroxide (1 g, containing 10% osmium tetroxide) were added, and the mixture was stirred at 40 to 50° C. for 21 hours. Insoluble microcapsulated osmium tetroxide was removed by filtration, and was washed with acetonitrile, and the filtrate was concentrated under reduced pressure. The residue was purified by flash column chromatography on silica gel (hexane:ethyl acetate=1:1) to obtain the title compound (4.97 g) as a colorless solid.

後処理

  1. customInsoluble microcapsulated osmium tetroxide was removed by filtration
  2. washwas washed with acetonitrile
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe residue was purified by flash column chromatography on silica gel (hexane:ethyl acetate=1:1)

出典と根拠

ORDレコード
ord-a208a3bfb2bf47e1bdb62b32909e450c
出典データセット
uspto-grants-2007_03
特許番号
US07192968B2

反応ノート

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