Water → cis-1,2-Cyclooctanediol

HRID 2104357ノート

反応式

HRID 2104357 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 were added N-methylmorpholine N-oxide (5.15 g), microencapsulated osmium tetraoxide (1 g, 10% osmium tetraoxide content), followed by stirring at 40-50° C. for 21 hours. Any insoluble microencapsulated osmium was filtered off, and was washed with acetonitrile. The filtrate was concentrated under reduced pressure, and the residue was purified by silica gel flash column chromatography (hexane:ethyl acetate=1:1), to thereby give the title compound (4.97 g).

後処理

  1. filtrationAny insoluble microencapsulated osmium was filtered off
  2. washwas washed with acetonitrile
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customthe residue was purified by silica gel flash column chromatography (hexane:ethyl acetate=1:1)

出典と根拠

ORDレコード
ord-4af616c19fea4bdabdafcb62035d3786
出典データセット
uspto-grants-2009_08
特許番号
US07576135B2

反応ノート

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