Hexane → 3,4-Dihydro-2-naphthalenylacetonitrile

HRID 330275

반응식

HRID 330275 반응식
CCCCCC.[H-].[Na+].[C:9]([CH2:11]P(=O)(OCC)OCC)#[N:10].[CH2:20]1[C:29](=O)[CH2:28][C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH2:21]1>C1COCC1.O>[C:21]1([CH2:11][C:9]#[N:10])[C:22]2[C:27](=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:28][CH2:29][CH:20]=1

참가 물질

7

반응물 4

HCID 8058HexaneHCID 24758Sodium hydrideHCID 682662-TetraloneHCID 75676Diethyl (cyanomethyl)phosphonate

생성물 1

HCID 27778183,4-Dihydro-2-naphthalenylacetonitrile수율 79%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매2회

실험 절차

To a mechanically stirred mixture of hexane washed sodium hydride (8.98 g, 0.187 mol, 50%/mineral oil) in THF (400 mL) was added diethyl cyanomethylphosphonate (33.13 g, 0.187 mol) dropwise. The reaction was stirred at room temperature for 1/2 hour. β-Tetralone (24.8 g, 0.170 mol) in THF (100 mL) was added dropwise at 0° C., and the reaction was stirred at room temperature for 1 hour. The reaction was diluted with water (600 mL) and extracted with ether (3×400 mL). The organic phase was washed with brine, dried (MgSO4), and concentrated under reduced pressure to give an orange oil. Distillation from bulb to bulb under high vacuum yielded 22.65 g (79%) of product as a pale yellow oil.

후처리

  1. stirringthe reaction was stirred at room temperature for 1 hour
  2. extractionextracted with ether (3×400 mL)
  3. washThe organic phase was washed with brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated under reduced pressure
  6. customto give an orange oil
  7. distillationDistillation from bulb to bulb under high vacuum

출처 및 근거

ORD 기록
ord-5d5b182bb2b5485f9bd2ebb037d9f587
출처 데이터셋
uspto-grants-1990_01
특허 번호
US04895860

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