Diethyl Ether → HCID 85971407, 화합물

HRID 530239노트

반응식

HRID 530239 반응식
[CH3:1][C:2]1[CH2:6][CH2:5][C:4]([CH3:8])([CH3:7])[C:3]=1[C:9]#N.[H-].C([Al+]CC(C)C)C(C)C.C([O:23]CC)C>ClCCl>[CH3:1][C:2]1[CH2:6][CH2:5][C:4]([CH3:8])([CH3:7])[C:3]=1[CH:9]=[O:23]

참가 물질

5

반응물 3

HCID 3283Diethyl EtherHCID 21225700DiisobutylaluminumhydrideHCID 217652822,5,5-Trimethylcyclopent-1-ene-1-carbonitrile

생성물 1

HCID 85971407HCID 85971407, 화합물수율 68%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a stirred solution of the product of Example 8g (600 mg, 4.44 mmol) in anhydrous dichloromethane (30 mL) at −78° C. under argon was added diisobutyl aluminum hydride (1.0 M in hexane, 8.9 mL, 8.9 mmol). The reaction was kept at −78° C. for 2 hours. The mixture was diluted with diethyl ether (150 mL) and quenched by addition of wet sodium sulfate. The mixture was then stirred for 30 minutes, filtered and the filtrate concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: petroleum ether/ethyl acetate=50/1->20/1) to afford the title compound as a light yellow liquid (420 mg, Yield: 68%). 1H NMR (400 MHz, CDCl3) δ 9.98 (s, 1H), 2.45 (t, J=7.4 Hz, 2H), 2.10 (s, 3H), 1.67 (t, J=7.4 Hz, 2H), 1.22 (s, 6H) ppm.

후처리

  1. customquenched by addition of wet sodium sulfate
  2. filtrationfiltered
  3. concentrationthe filtrate concentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (eluent: petroleum ether/ethyl acetate=50/1->20/1)

출처 및 근거

ORD 기록
ord-a1a5d71c83d0497983eee72486e73be8
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09353063B2

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