Diethyl Ether → HCID 85971407、化合物

HRID 530239ノート

反応式

HRID 530239 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

HCID 85971407HCID 85971407、化合物収率 68%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-a1a5d71c83d0497983eee72486e73be8
出典データセット
uspto-grants-2016_05
特許番号
US09353063B2

反応ノート

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