Water → cis-1,2-Cycloheptanediol

HRID 546424

反応式

HRID 546424 の反応式
[CH:1]1CC[CH2:5][CH2:4][CH2:3][CH:2]=1.C[N+]1([O-])[CH2:14][CH2:13][O:12]CC1.[OH2:16]>C(#N)C.[Os](=O)(=O)(=O)=O>[C@@H:13]1([OH:12])[CH2:14][CH2:5][CH2:4][CH2:3][CH2:2][C@@H:1]1[OH:16]

参加物

6

反応物 3

HCID 962WaterHCID 12363CyclohepteneHCID 82029Methyl morpholine oxide

生成物 1

HCID 11768603cis-1,2-Cycloheptanediol

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

Cycloheptene (3.85 g) was dissolved in acetonitrile (45 ml) and water (15 ml), and to the solution N-methylmorpholine N-oxide (5.15 g), microcapsulated osmium tetroxide (1 g, containing 10% osmium tetroxide) was added, and the mixture was stirred at 40 to 50° C. for 21 hours. Insoluble microcapsulated osmium tetroxide was removed by filtration, and the insoluble substance 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 (4.77 g) as a colorless solid.

後処理

  1. customInsoluble microcapsulated osmium tetroxide was removed by filtration
  2. washthe insoluble substance was 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-41bcfb5306e748c4b762f62d5f559c8b
出典データセット
uspto-grants-2011_05
特許番号
US07935824B2

関連ノート

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