Hexane → Benzofuran-3-acetonitrile

HRID 330288

반응식

HRID 330288 반응식
CCCCCC.[H-].[Na+].[C:9]([CH2:11]P(=O)(OCC)OCC)#[N:10].[O:20]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[C:22](=O)[CH2:21]1>C1COCC1.O>[O:20]1[C:28]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[C:22]([CH2:11][C:9]#[N:10])=[CH:21]1

참가 물질

7

반응물 4

HCID 8058HexaneHCID 23556CoumaranoneHCID 24758Sodium hydrideHCID 75676Diethyl (cyanomethyl)phosphonate

생성물 1

HCID 2769401Benzofuran-3-acetonitrile수율 101%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매2회

실험 절차

To a stirred mixture of hexane washed sodium hydride (2.21 g, 0.046 mol, 50%/mineral oil) in THF (125 mL), was added diethyl cyanomethylphosphonate (8.15 g, 0.046 mol) dropwise. The reaction was stirred at room temperature for 1/2 hour, 3-coumaranone (sublimed) (5.6 g, 0.042 mol) in THF (100 mL) was added dropwise at 0° C., and the reaction mixture was stirred at room temperature overnight. The mixture was diluted with water (300 mL), and extracted with ether (800 mL). The extracts were washed with brine (2×100 mL), dried (MgSO4), and concentrated to yield 6.67 g (100%) of the product as an off-white solid.

후처리

  1. stirringthe reaction mixture was stirred at room temperature overnight
  2. extractionextracted with ether (800 mL)
  3. washThe extracts were washed with brine (2×100 mL)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-b3c4eebd609749fc9e0e82105e841106
출처 데이터셋
uspto-grants-1990_01
특허 번호
US04895860

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