3,4-dihydro-2H-pyran → 2-(4-Bromobutoxy)tetrahydro-2H-pyran

HRID 6588

反応式

HRID 6588 の反応式
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][OH:6].[O:7]1[CH:12]=[CH:11][CH2:10][CH2:9][CH2:8]1.C(=O)([O-])[O-].[K+].[K+]>ClCCl.P(Cl)(Cl)(Cl)=O>[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][O:6][CH:8]1[CH2:9][CH2:10][CH2:11][CH2:12][O:7]1

参加物

6

反応物 3

HCID 80803,4-dihydro-2H-pyranHCID 11430Potassium CarbonateHCID 1183884-Bromobutanol

生成物 1

HCID 5590192-(4-Bromobutoxy)tetrahydro-2H-pyran

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 24813Phosphorus oxychloride溶媒

実験手順

To a solution of commercially available 4-bromobutan-1-ol (16) (1 equi.) and 3,4-dihydropyran (17) (1.5 equi.) in dichloromethane (3 mL/mmole), phosphorus oxychloride (0.01 equi.) was added at room temperature. The reaction mixture was stirred at that temperature for 24 h. Then potassium carbonate (1 equi.) was added to the reaction mixture and the reaction mixture was stirred at room temperature for 1 h, quenched with water, extracted with dichloromethane, washed with brine, dried over MgSO4, and concentrated in vacuo. Purification by chromatography on silica gel (5% EtOAc (ethylacetate)/hexanes) afforded 2-(4-bromobutoxy) -tetrahydropyran (18), as a colorless oil (88%).

後処理

  1. stirringthe reaction mixture was stirred at room temperature for 1 h
  2. customquenched with water
  3. extractionextracted with dichloromethane
  4. washwashed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customPurification by chromatography on silica gel (5% EtOAc (ethylacetate)/hexanes)

出典と根拠

ORDレコード
ord-9c10f800168b48649bfb59f8e3d09d94
出典データセット
uspto-grants-2006_08
特許番号
US07083832B2

関連ノート

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