Isopropanol → 4-Pentylcyclohexanal

HRID 48104

反応式

HRID 48104 の反応式
[CH2:1]([CH:6]1[CH2:11][CH2:10][CH:9]([CH2:12][OH:13])[CH2:8][CH2:7]1)[CH2:2][CH2:3][CH2:4][CH3:5].C(=O)([O-])[O-].[K+].[K+].I([O-])(=O)(=O)=O.[Na+].CC(O)C>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.C(Cl)(Cl)Cl.O.[Ru](Cl)(Cl)Cl>[CH2:1]([CH:6]1[CH2:7][CH2:8][CH:9]([CH:12]=[O:13])[CH2:10][CH2:11]1)[CH2:2][CH2:3][CH2:4][CH3:5]

参加物

8

反応物 4

HCID 3776IsopropanolHCID 11430Potassium CarbonateHCID 13548135(4-Pentylcyclohexyl)methanolHCID 23667635Sodium periodate

生成物 1

HCID 140856594-Pentylcyclohexanal収率 83%

試薬・触媒・溶媒 3

HCID 66133Benzyl triethylammonium chloride触媒HCID 61850Ruthenium trichloride溶媒HCID 22418719Chloroform water溶媒

実験手順

To a slurry of (4-pentyl-cyclohexyl)-methanol (21) (1 equi.), benzyltriethylammonium chloride (0.05 equi.), potassium carbonate (0.15 equi.), and sodium periodate (1.5 equi.) in chloroform-water (1:1) (2 mL/mmole), ruthenium chloride (0.03 equi.) was added at room temperature. The reaction mixture was stirred at 60 C for 2 h. 2-Propanol (0.3 equi.) was added and the reaction mixture was stirred for another 30 min at 60 C, cooled to room temperature, filtered through celite, extracted with dichloromethane, dried over MgSO4, and concentrated in vacuo. Purification by chromatography on silica gel (dichloromethane) afforded 4-pentyl-cyclohexanecarboxaldehyde (22) as a colorless oil (83%).

後処理

  1. stirringthe reaction mixture was stirred for another 30 min at 60 C
  2. filtrationfiltered through celite
  3. extractionextracted with dichloromethane
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customPurification by chromatography on silica gel (dichloromethane)

出典と根拠

ORDレコード
ord-ad38f816235d4afa8e8eceaba7c1ce9e
出典データセット
uspto-grants-2004_03
特許番号
US06703082B1

関連ノート

読み込み中…